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[ CAS No. 2516-47-4 ] {[proInfo.proName]}

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Chemical Structure| 2516-47-4
Chemical Structure| 2516-47-4
Structure of 2516-47-4 * Storage: {[proInfo.prStorage]}

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Product Details of [ 2516-47-4 ]

CAS No. :2516-47-4 MDL No. :MFCD00037147
Formula : C4H9N Boiling Point : No data available
Linear Structure Formula :CH2CH2CHCH2NH2 InChI Key :IGSKHXTUVXSOMB-UHFFFAOYSA-N
M.W : 71.12 Pubchem ID :75646
Synonyms :
Chemical Name :Cyclopropylmethylamine

Calculated chemistry of [ 2516-47-4 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 5
Num. arom. heavy atoms : 0
Fraction Csp3 : 1.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 21.94
TPSA : 26.02 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.71 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.36
Log Po/w (XLOGP3) : 0.03
Log Po/w (WLOGP) : 0.29
Log Po/w (MLOGP) : 0.35
Log Po/w (SILICOS-IT) : 0.72
Consensus Log Po/w : 0.55

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 3.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -0.23
Solubility : 41.5 mg/ml ; 0.584 mol/l
Class : Very soluble
Log S (Ali) : -0.13
Solubility : 52.9 mg/ml ; 0.743 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.38
Solubility : 29.4 mg/ml ; 0.414 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.0

Safety of [ 2516-47-4 ]

Signal Word:Danger Class:3,8
Precautionary Statements:P210-P280-P305+P351+P338-P310 UN#:2733
Hazard Statements:H225-H314 Packing Group:Ⅱ
GHS Pictogram:

Application In Synthesis of [ 2516-47-4 ]

* 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.

  • Downstream synthetic route of [ 2516-47-4 ]

[ 2516-47-4 ] Synthesis Path-Downstream   1~10

  • 1
  • [ 1121-60-4 ]
  • [ 67-56-1 ]
  • [ 10521-08-1 ]
  • [ 2516-47-4 ]
  • N-Cyclopropylmethyl-2,6-di<2>pyridyl-4-piperidon-3-carbonsaeuremethylester [ No CAS ]
  • 2
  • [ 31872-62-5 ]
  • [ 2516-47-4 ]
  • [ 842143-89-9 ]
YieldReaction ConditionsOperation in experiment
In ethanol; at 85℃; for 48h; 4-METHOXY-3-NITROPYRIDINE (10.0 g, 64 MMOL), cyclopropylmethyl amine (4.56 g, 64 MMOL), and EtOH (7 mL) were combined in a sealed tube and heated to 85 °C with vigourous shaking for 48 h. The mixture was concentrated in vacuo to afford the desired compound as a solid (12.0 g). MS (ES+) m/z 194 [M+H] +.
  • 3
  • [ 106157-91-9 ]
  • [ 2516-47-4 ]
  • [ 50607-30-2 ]
  • 2-(2-Amino-pyrimidin-4-yl)-1-cyclopropylmethyl-1,5,6,7-tetrahydro-pyrrolo[3,2-c]pyridin-4-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
49% In ethanol; at 70℃; for 3h; EXAMPLE 59 2-(2-Amino-pyrimidin-4-yl)-1-cyclopropylmethyl-1,5,6,7-tetrahydro-pyrrolo[3,2-c]pyridin-4-one A mixture of 1-(2-aminopyrimidin-4-yl)-2-bromoethanone hydrobromide (0.9 g, 3 mmol), cyclopropylmethylamine (0.85 g, 12 mmol, 1.03 mL) and <strong>[50607-30-2]piperidin-2,4-dione</strong> (0.51 g, 4.5 mmol), dissolved in absolute ethanol (10 mL), was stirred under heating at 70° C. for 3 hours in a glass pressure tube. Ethanol was evaporated off and the crude reaction mixture was purified by flash chromatography on silica gel (eluant: DCM/MeOH 4:1) and then by crystallization from MeOH. The title compound was obtained as white solid (0.42 g, 49percent yield). 1H NMR (400 MHz, DMSO-D6) delta ppm 0.30-0.48 (m, 4 H) 1.12-1.26 (m, 1 H) 2.97 (t, J=6.77 Hz, 2 H) 3.45 (t, J=6.46 Hz, 2 H) 4.61 (d, J=7.07 Hz, 2 H) 7.34-7.44 (d, J=6.95Hz, 1 H and one s, 1H) 7.71 (s, 1 H) 8.15 (d, J=6.95 Hz, 1 H) 8.31 (s, 1 H).
  • 4
  • [ 149057-19-2 ]
  • [ 2516-47-4 ]
  • [ 1311150-59-0 ]
  • 5
  • [ 3012-80-4 ]
  • [ 24424-99-5 ]
  • [ 2516-47-4 ]
  • [ 1429383-54-9 ]
YieldReaction ConditionsOperation in experiment
Step A. tert-Bu yl cyclopropylmethyl((l-methyl-lH-benzo[d]imidazol-2- yl)methyl)carbamate To a mixture of [1 -methyl- lH-benzo[d]imidazole-2-carbaldehyde (1.78 g, 11.11 mmol) and cyclopropylmethanamine (0.790 g, 11.1 1 mmol) was added a 2 mL of anhydrous acetonitrile and the solvent was removed under reduced pressure on a rotary evaporator. This precedure was repeated several times until a chalky solid was obtained. This was then dissolved in 100 mL of DCM, cooled to 0 C, and NaBH(OAc)3 (3.53 g, 16.67 mmol) was added in one portion. After 30 min, the mixture was re-cooled to 0 C and then triethylamine (4.65 mL, 33.3 mmol) and di-ieri-butyl dicarbonate (2.91 g, 13.34 mmol) were added. The reaction mixture was allowed to warm to ambient temperature overnight, at which time it was quenched by addition of 100 mL of water and extracted with DCM (100mLx2). The combined organic layers were dried over Na2S04, filtered and the filtrate was concentrated under reduced pressure. The residue was suspended in acetonitrile and filtered to remove insoluble impurities. The filtrate was concentrated under reduced pressure. Purification of the residue by flash chromatography on silica gel (eluent: 0 to 25% EtOAc/hexane) provided the title compound. Mass Spectrum (ESI) m/z = 316 (M+l).
  • 6
  • [ 1006-68-4 ]
  • [ 2516-47-4 ]
  • [ 1552274-18-6 ]
YieldReaction ConditionsOperation in experiment
250 mg With trifluoroacetic acid; In 1,2-dichloro-benzene; at 200℃; for 1.5h;Microwave irradiation; 1-(Cyclopropylmethyl)-5-phenyl-1H-imidazole (EV-AS5429-002)- Step 1 To a solution of <strong>[1006-68-4]5-phenyl-1,3-oxazole</strong> (CAS 1006-68-4, 1.00 g, 6.90 mmol) and cyclopropyl-methylamine (CAS 2516-47-4, 980 mg, 13.8 mmol) in o-dichlorobenzene (10 ml) was added trifluoroacetic acid (1.054 ml, 13.78 mmol). The reaction was stirred at 200C under microwave irradiation for 1.5h. The mixture was poured into a mixture of 1M aqueous sodium hydroxide (20 ml) and saturated aqueous sodium chloride (40 ml) and extracted with ethyl acetate (3x20 ml). The combined organic extracts were dried over sodium sulfate and concentrated in vacuo. The crude material was purified with an SCX-II cartridge. The cartridge was washed sequentially with MeOH then with 2M ammonia in MeOH. The ammonia/MeOH washings were concentrated in vacuo to obtain 250 mg of 1-(cyclopropylmethyl)-5-phenyl-1H- imidazole (EV-AS5429-002) as a brown solid. LCMS (method D): retention time 0.71min, M/z = 199 (M + 1).
  • 7
  • [ 408328-13-2 ]
  • [ 2516-47-4 ]
  • 6-bromo-N-(cyclopropylmethyl)benzo[d]thiazol-2-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
67% In 1,4-dioxane; at 80℃; for 12h; General procedure: A mixture of <strong>[408328-13-2]2,6-dibromobenzo[d]thiazole</strong> (293 mg, 1.00 mmol) and corresponding amine (3 eq) in1,4-dioxane (3 mL) was heated to 80 C overnight. After cooling to room temperature, the solvent was removed by vacuum and the resulting residue was dissolved in ethyl acetate (50 mL), and washed with brine (10 mL * 3). The organic layer was dried over Na2SO4, and concentrated in vacuum to give the desired product.
  • 8
  • [ 133446-99-8 ]
  • [ 2516-47-4 ]
  • 2-(cyclopropylmethyl)-5-nitro-2,3-dihydro-1H-isoindol-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
1 g In tetrahydrofuran; for 8h;Reflux; 2-Bromo-4-nitro - benzoic acid methyl ester (2 g, 10.9 mmol) wasdissolved in tetrahydrofuran (6 mL), and under ice cooling was added dropwisethereto cyclopropylmethyl amine (1 g, 14.1 mmol), the addition was complete thereaction was heated at reflux for 8 hours. The reaction mixture was cooledto room temperature to precipitate a white solid, the filter cake washed with alittle ethanol and dried to obtain2-cyclopropylmethyl-methyl-5-nitro-2,3-dihydro-- isoindol-1-one (yellow Thesolid, 1 g).
  • 9
  • [ 35344-95-7 ]
  • [ 2516-47-4 ]
  • C8H11N3 [ No CAS ]
  • 10
  • [ 579514-75-3 ]
  • [ 2516-47-4 ]
  • C15H20N2O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; In ethanol; General procedure: To a solution fo <strong>[579514-75-3]tert-butyl 4-fluoro-3-nitrobenzoate</strong> (560 mg, 2.3 mmol) in 20mL of EtOH were added butan-1-amine (853 mg, 11.6 mmol) and stirred at rt for 2 h.The reaction mixture was concentrated to dryness, and the residue was dissolved inEtOAc (10 x 3 mL) and washed with brine (10 mL). The combined organic layerswere dried over MgSO4, and concentrated in vacuo to afford the product tert-butyl 4-(butylamino)-3-nitrobenzoate (35b) as yellow-orange solid (490 g, 72% yield).
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