Purity | Size | Price | VIP Price | USA Stock *0-1 Day | Global Stock *5-7 Days | Quantity | ||||||
{[ item.p_purity ]} | {[ item.pr_size ]} | Inquiry |
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,1,item.pr_is_large_size_no_price) ]} |
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price) ]} | Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate,item.pr_is_large_size_no_price) ]} | {[ item.pr_usastock ]} | in stock Inquiry - | {[ item.pr_chinastock ]} | {[ item.pr_remark ]} in stock Inquiry - | Login | Inquiry |
Please Login or Create an Account to: See VIP prices and availability
CAS No. : | 115652-52-3 | MDL No. : | MFCD09834330 |
Formula : | C4H10ClNO | Boiling Point : | No data available |
Linear Structure Formula : | - | InChI Key : | ULEMJGCUGKDKTD-UHFFFAOYSA-N |
M.W : | 123.58 | Pubchem ID : | 14146222 |
Synonyms : |
|
Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | |
Hazard Statements: | H302-H315-H319-H332-H335 | Packing Group: | |
GHS Pictogram: |
![]() |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; In 1,4-dioxane; at 20℃; | 8.2 1-aminocyclopropanemethanol 1.04 g tert-butyl (1-hydroxymethylcyclopropyl)-carbamidate are placed in 5 ml dioxane. 2.5 ml HCl in dioxane (4 mol/l) are added dropwise. The reaction mixture is stirred for 15 h at ambient temperature. The solvent is evaporated down by half and the precipitated solid is suction filtered. 0.5 g product are obtained as the hydrochloride. 1H NMR (400 MHz, DMSO): 5.27 (1H, t); 0.91 (2H, t); 0.71 (2H, t). | |
With hydrogenchloride; In 1,4-dioxane; at 20℃; for 0.25h; | 2.2 1-aminocyclopropanemethanol 1.04 g tert-butyl (1-hydroxymethylcyclopropyl)-carbamidate are placed in 5 ml dioxane. 2.5 ml HCl in dioxane (4 mol/l) are added dropwise. The reaction mixture is stirred for 15 h at ambient temperature. The solvent is evaporated down by half and the precipitated solid is suction filtered. 0.5 g product are obtained as the hydrochloride. 1H NMR (400 MHz, DMSO): 5.27 (1H, t); 0.91 (2H, t); 0.71 (2H, t). | |
With hydrogenchloride; In 1,4-dioxane; at 20℃; | 1.3.2 1-aminocyclopropanemethanol 1.04 g tert-butyl (1-hydroxymethylcyclopropyl)-carbamidate are placed in 5 ml dioxane. 2.5 ml HCl in dioxane (4 mol/l) are added dropwise. The reaction mixture is stirred for 15 h at ambient temperature. The solvent is evaporated down by half and the precipitated solid is suction filtered. 0.5 g product are obtained as the hydrochloride. 1H NMR (400 MHz, DMSO): 5.27 (1H, t); 0.91 (2H, t); 0.71 (2H, t). |
With hydrogenchloride; In 1,4-dioxane; at 20℃; for 15h; | 4.2 1-aminocyclopropanemethanol1.04 g tert-butyl (1-hydroxymethylcyclopropyl)-carbamidate are placed in 5 ml dioxane. 2.5 ml HCl in dioxane (4 mol/l) are added dropwise. The reaction mixture is stirred for 15 h at ambient temperature. The solvent is evaporated down by half and the precipitated solid is suction filtered. 0.5 g product are obtained as the hydrochloride.1H NMR (400 MHz, DMSO): 5.27 (1H, t); 0.91 (2H, t); 0.71 (2H, t). | |
0.5 g | With hydrogenchloride; In 1,4-dioxane; at 20℃; for 15h; | 8.2 1-aminocyclopropanemethanol 1.04 g tert-butyl (1-hydroxymethylcyclopropyl)-carbamidate are placed in 5 ml dioxane. 2.5 ml of HCl in dioxane (4 mol/l) are added dropwise. The reaction mixture is stirred for 15 h at ambient temperature. The solvent is evaporated down by half and the precipitated solid is suction filtered. 0.5 g product are obtained as the hydrochloride. 1H NMR (400 MHz, DMSO): 5.27 (1H, t); 0.91 (2H, t); 0.71 (2H, t). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 0.5h; | Example 37; 6-(4-Chloro-phenyl)-5-(2-methoxy-ethoxy)-pyrazine-2-carboxylic acid (1-hydroxymethyl-cyclopropyl)-amide; To a suspension of 0.05 g (0.00016 mol) of 6-(4-chloro-phenyl)-5-(2-methoxy-ethoxy)-pyrazine-2-carboxylic acid in 2.0 ml dichloromethane was added 0.024 g 1-chloro-N,N,2-trimethyl-1-propenylamine and the mixture was stirred at room temperature for 30 min. To the resulting slightly brown solution was added 0.040 g of <strong>[115652-52-3](1-amino-cyclopropyl)-methanol hydrochloride</strong> and dropwise 0.1 ml N-ethyldiisopropyl-amine. The mixture was stirred at ambient temperature for 30 min. The resulting mixture was partitioned between 10percent aqueous citric acid and ethyl acetate. The phases were separated and the organic phase was dried over magnesium sulfate and evaporated. The residue was purified by chromatography on silica gel using a gradient of heptane to ethyl acetate to yield 0.035 g (55percent yield) of the title compound as off white solid. MS (ISP) (M+H+)=378.3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
11% | In N,N-dimethyl-formamide; at 90℃; for 18h; | 5-amino-4-(3,4-dichlorophenyl)-2-(methylsulfinyl) thiopheno[2,3-d]pyrimidine-6- carboxamide (30 mg, 0.75 mmol), (aminocyclopropyl) methan-1-ol hydrochloride (500 mg, <n="205"/>4.0 mmol, prepared according to Kiely et al. J. Med. Chem. (1988), 31(10), 2004-8.), DIEA (3.0 mL, 18 mmol) and DMF (10 mL) were combined and heated at 90 0C for 18hours. The solvents were evaporated, the residue was dissolved in DMSO (4 mL), and the product was purified using reverse-phase preparative HPLC (25-60percent acetonitrile, 0.1percent TFA, 30min). The appropriate fractions were combined and concentrated on a rotary evaporator. The residue was dissolved in ethyl acetate (100 mL), washed with aqueous NaHCC3, and dried over Na2SO4. The solvent was removed in vacuo to give 35 mg (1 1percent) of product as a light yellow solid. 1H NMR (400 MHz, D6-DMS0) delta ppm 8.04 (bs, IH), 7.85 (s, IH), 7.79 (d, IH, J= 7.6 Hz), 7.58 (m, IH), 7.04 (s, 2H), 6.14 (bs, 2H), 4.72 (t, IH, J = 6 Hz), 3.58 (m, 2H), 0.80 (m, 2H), 0.67 (m, 2H). MS m/z calculated for (M + H)+ 424, found 424. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; at 160℃; | 2.3 [1-(2-chloro-6,7-dihydrothieno[3,2-d]pyrimidin-4-ylamino)-cyclopropyl]-methanol (III-2) 1.4 g (II) are placed in 10 ml dioxane, then 3.6 ml diisopropylethylamine and then 1 g of 1-aminocyclopropanemethanol (see 2.2) are added. The reaction mixture is heated to 160° C., until there is no further reaction, and cooled, then evaporated down. The residue is treated with cyclohexane/ethyl acetate (4:1) in the ultrasound bath, the solid is suction filtered and dried. 1.24 g (III-2) are obtained as a solid. Analytical HPLC-MS (method A): RT=1.01 min. | |
With N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; at 160℃; | 1.3.3 [1-(2-chloro-6,7-dihydrothieno[3,2-d]pyrimidin-4-ylamino)-cyclopropyl]-methanol (III-2) 1.4 g (II) are placed in 10 ml dioxane, then first 3.6 ml diisopropylethylamine are added, followed by 1 g of 1-aminocyclopropanemethanol (see 1.3.2). The reaction mixture is heated at 160° C, until no further reaction takes place, and after cooling, evaporated down. The residue is treated with cyclohexane/ethyl acetate (4:1) in the ultrasound bath and the solid is suction filtered and dried. 1.24 g (III-2) are obtained as a solid. Analytical HPLC-MS (method B): RT=1.01 min. | |
1.24 g | With N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; at 160℃; | 8.3 [1-(2-chloro-6,7-dihydrothieno[3,2-d]pyrimidin-4-ylamino)-cyclopropyl]-methanol (III-4) 1.4 g (II) are placed in 10 ml dioxane, first 3.6 ml diisopropylethylamine, then 1 g of 1-aminocyclopropanmethanol (see 8.2) are added. The reaction mixture is heated to 160° C. until there is no further reaction and after cooling evaporated down. The residue is treated with cyclohexane/ethyl acetate (8:2) in the ultrasound bath and the solid is suction filtered and dried. 1.24 g (III-4) are obtained as a solid. Analytical HPLC-MS (method A): RT=1.01 min. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 2h; | Step 9: (9H-fluoren-9-yl)methyl (R)-3-((R)-2-dodecanamido-3-(hexadecyloxy)propylthio)-l-(l- (hydroxymethyl)cyclopropylamino)-l-oxopropan-2-ylcarbamate[000448] To a solution of (5No.,9No.)-9-dodecanamido-l-(9H-fluoren-9-yl)-3-oxo-2,l l-dioxa-7- thia-4-azaheptacosane-5-carboxylic acid (1 eq) and HBTU (1.2 eq) in DCM (0.06 M) was added DIEA (3.5 eq), followed by (1-aminocyclopropyl) methanol hydrochloride (1.2 eq). The reaction was stirred at room temperature for 2 hr. The crude mixture was purified by flash chromatography on a COMBIFLASH.(R). system (ISCO) using 30-50percent EtOAc/Hex to give (9H-fluoren-9-yl)methyl (R)-3-((R)-2-dodecanamido-3-(hexadecyloxy)propylthio)-l-(l- (hydroxymethyl)cyclopropylamino)-l-oxopropan-2-ylcarbamate. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 2h; | Step 9: Benzyl (R)-3-((R)-2,3-didodecanamidopropylthio)-l-(l-(hydroxymethyl)cyclopropyl amino)- 1 -oxopropan-2-ylcarbamate[000458] To a solution of (5",9")-9-dodecanamido-3,12-dioxo-l-phenyl-2-oxa-7-thia-4,l 1- diazatricosane-5-carboxylic acid (1 eq) in DCM (0.1 M) was added (1-aminocyclopropyl) methanol hydrochloride (1.3 eq), DIEA (2.5 eq) and HBTU (1.2 eq). The reaction was stirred at room temperature for 2 hours then concentrated and purified by flash chromatography on aCOMBIFLASH.(R). system (ISCO) using a gradient of 0-100percent EtOAc/Hex, then 0-10percentMeOH/DCM to afford the title compound as an off-white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 2h; | Example 1Synthesis of: (/?)-3-((/?)-2-amino-3-(l-(hvdroxymethyl)cvclopropylamino)-3-oxopropylthio) propane- 1,2-diyl didodecanoateStep 1: (R)-3-((R)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-(l-(hydroxymethyl)cyclo- propylamino)-3-oxopropylthio)propane-l,2-diyl didodecanoate[000398] To a solution of (5",9")-9-(dodecanoyloxy)-l-(9H-fluoren-9-yl)-3,12-dioxo-2,l l- dioxa-7-thia-4-azatricosane-5-carboxylic acid (6, 1 eq) and HBTU (1.2 eq) in DCM (0.06 M) was added DIEA (3.5 eq), followed by (1-aminocyclopropyl) methanol hydrochloride (1.2 eq). The reaction was stirred at room temperature for 2 hours. The crude mixture was purified by flash chromatography on a COMBIFLASH.(R). system (ISCO) using 30-50percent EtO Ac/Hex to give (R)-3- ((R)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-(l-(hydroxymethyl)cyclopropylamino)-3- oxopropylthio)propane- 1 ,2-diyl didodecanoate. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
32.8% | EXAMPLE 104: 5-(7-Fluoropyrazolo[4,3-b]indol-4(lH)-yl)-N-(1-(hydroxymethyl)cyclopropyl)-4-methylpicolinamide [0535] 5-(7-Fluoro-l-(tetrahydro-2H-pyran-2-yl)pyrazolo[4,3-]indol-4(lH)-yl)-4- methylpicolinic acid (30 mg, 0.076 mmol), (l-aminocyclopropyl)methanol hydrochloride (18.80 mg, 0.152 mmol), HATU (34.7 mg, 0.091 mmol), DIPEA (0.040 mL, 0.228 mmol) and DMF (1 mL) were mixed in a 4 mL vial equipped with a magnetic stir bar. The resulting brown solution was stirred overnight. The reaction mixture was partitioned between water (10 mL) and EtOAc (20 mL). The layers were separated and the aqueous layer was back- extracted with EtOAc (20 mL). The combined organic layers were concentrated to yield a dark syrup, which was dissolved in MeOH (3 mL), treated with concentrated HC1 (3 drops), and stirred overnight. The product was purified by preparative HPLC, eluting with 25-50percent ACN in water (containing 0.05percent TFA). The pure fractions were lyophilized to give a TFA salt of the title compound as a light yellow solid (12.3 mg, 32.8percent). 1H NMR (400 MHz, DMSO-de) delta ppm 0.80 (s, 3 H), 1.01 (d, J=17.68 Hz, 1 H), 2.21 (s, 3 H), 3.54 (s, 2 H), 7.11 - 7.18 (m, 2 H), 7.64 - 7.66 (m, 1 H), 7.69 (dd, J=9.09, 2.53 Hz, 1 H), 8.16 (s, 1 H), 8.64 (s, 1 H), 8.81 (s, 1 H). MS [M+H]+ calc'd for C2oHi8FN502, 380.15; found 380.4. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
14% | EXAMPLE 100: 5-(7-Fluoropyrazolo[4,3-b]indol-4(1H)-yl)-N-(1-(hydroxymethyl)cyclopropyl)-6-methylpicolinamide [0527] 5-(7-Fluoro-l-(tetrahydro-2H-pyran-2-yl)pyrazolo[4,3-]indol-4(lH)-yl)-6- methylpicolinic acid (30 mg, 0.076 mmol), (l-aminocyclopropyl)methanol hydrochloride (18.80 mg, 0.152 mmol), HATU (34.7 mg, 0.091 mmol), DIPEA (0.040 mL, 0.228 mmol) and DMF (1 mL) were mixed in a 4 mL vial equipped with a magnetic stir bar. The resulting brown solution was stirred overnight. The reaction mixture was partitioned between water (10 mL) and EtOAc (20 mL). The layers were separated and the aqueous layer was back- extracted with EtOAc (20 mL). The combined organic layers were concentrated to yield a dark syrup, which was dissolved in MeOH (3 mL) and treated with concentrated HC1 (3 drops). The mixture was stirred overnight and subsequently purified by preparative HPLC, eluting with 25-50percent ACN in water (containing 0.05percent TFA). The pure fractions were lyophilized to give a TFA salt of the title compound as a light yellow solid (5.3 mg, 14percent). 1H NMR (400 MHz, DMSO-d6) delta ppm 0.82 (s, 4 H), 2.37 (s, 3 H), 3.55 (s, 2 H), 7.14 - 7.18 (m, 2 H), 7.66 (s, 1 H), 7.70 (s, 1 H), 7.68 (s, 1 H), 8.00 - 8.06 (m, 2 H), 8.75 (s, 1 H). MS [M+H]+ calc'd for C2oHi8FN502, 380.15; found 380.4. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With triethylamine; In 1,4-dioxane; water; at 100℃; for 6.5h; | General procedure: General procedure B A solution of amino nucleophile (3 equiv.), triethylamine (10 equiv.), and Intermediate 1 (1 equiv.) was stirred in dioxane and water (2:1 ratio) at 90 °C until complete consumption of starting material was observed by LC/MS. The solution was diluted withiN hydrochloric acid and dichloromethane. The layers were then separated and thelayer was extracted with dichloromethane. The organics were combined, dried over magnesium sulfate, filtered, and the solvent was removed in vacuo. Purification yielded theproduct The title compound was prepared following general procedure B, except(1 -amino cyc lopropyl)methano 1 (as the HC1 salt) was the amine reactant, and the contents were heated to 100 °C for 6.5 h. The crude material was purified via silica gel chromatographyutilizing a 15percent acetonitrile-methanol (7:1) in dichloromethane gradient to deliver the desired compound, Compound 1-502 (54 mg, 90percent yield) as a white solid.1H-NMR (500 MHz, DMSO-d6) oe 9.10 (d, 1 H), 8.18 (d, 1 H), 8.00 (s, 1 H), 7.41 (s, 1 H), 7.33 (app. q, 1 H), 7.24-7.20 (m, 1 H), 7.22 (d, 1 H), 7.11 (app. t, 1 H), 6.89 (app. t, 1 H), 5.86 (s, 2 H), 4.89 (t, 1 H), 3.63 (d, 2 H), 0.85 (m, 2 H), 0.77 (m, 2 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
46% | Into a 500-mL round-bottom flask, was placed <strong>[115652-52-3](1-aminocyclopropyl)methanol hydrochloride</strong> (6 g, 48.55 mmol, 2 equiv), K2CO3 (11 g, 79.59 mmol, 3.5 equiv) in MeCN (120 mL), The mixture was stirred at room temperature for 10 min. This was followed by the addition of a solution of methyl 3-bromo-4-(bromomethyl)benzoate (15 g, 48.71 mmol, 1 equiv) in MeCN (150 mL) dropwise with stirring at 0° C. over 2h. The resulting solution was stirred overnight at room temperature. The resulting mixture was concentrated under vacuum. The residue was purified by silica gel chromatography (EtOAc/pet. ether, 1:3) to afford the title compound as a yellow oil (7 g, 46percent yield). MS: (ES, m/z): 314,316 [M+H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Intermediate: 5-((5-((3'-(3-bromopropoxy)-2'-chloro-2-methyl-[1,1'-biphenyl]-3-yl)methoxy)-4-chloro-2-(((1-(hydroxymethyl)cyclopropyl)amino)methyl)phenoxy)methyl)nicotinonitrile To a solution of 5-((5-((3'-(3-bromopropoxy)-2'-chloro-2-methyl-[1,1'-biphenyl]-3-yl)methoxy)-4-chloro-2-formylphenoxy)methyl)nicotinonitrile (20 mg, 0.031 mmol) in a mixture of 1,2-dichloroethanel (0.8 mL) and EtOH (0.5 mL) was added (1-aminocyclopropyl)methanol, HCl (12 mg, 0.097 mmol), acetic acid (3 muL, 0.052 mmol), and 4 A mol sieves. The reaction was flushed briefly with N2, capped, stirred at room temp for 90 min, then treated dropwise (over 1 h) with sodium cyanoborohydride, 1.0M in THF (65 muL, 0.065 mmol) and stirred at room temp for 18 h. Additional sodium cyanoborohydride (15 mulit) was added dropwise and the reaction was stirred at room temp for 1 h. N,N-diisopropylethylamine (15 muL) was added and the reaction stirred at room temp for 1.5 h. The solvent was removed under a gentle stream of N2 to give the title compound that was used "as is" without purification in subsequent reactions. LC/MS Condition A: ret time 1.18 min; m/e=710(M+H)+. |
[ 142733-65-1 ]
(cis-3-Aminocyclobutyl)methanol hydrochloride
Similarity: 0.68
[ 1504-49-0 ]
(trans-4-Aminocyclohexyl)methanol hydrochloride
Similarity: 0.68
[ 88887-87-0 ]
1-Methylcyclopropanamine hydrochloride
Similarity: 0.67
[ 845714-30-9 ]
(S)-2-Amino-2-cyclohexylethanol
Similarity: 0.65
[ 1041055-24-6 ]
(S)-2,6-Diaminohexan-1-ol dihydrochloride
Similarity: 0.74
[ 158741-04-9 ]
(R)-2-Aminohexan-1-ol hydrochloride
Similarity: 0.74
[ 1185-53-1 ]
2-Amino-2-(hydroxymethyl)propane-1,3-diol hydrochloride
Similarity: 0.73
[ 1041055-24-6 ]
(S)-2,6-Diaminohexan-1-ol dihydrochloride
Similarity: 0.74
[ 158741-04-9 ]
(R)-2-Aminohexan-1-ol hydrochloride
Similarity: 0.74
[ 1185-53-1 ]
2-Amino-2-(hydroxymethyl)propane-1,3-diol hydrochloride
Similarity: 0.73