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[ CAS No. 5337-03-1 ] {[proInfo.proName]}

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Chemical Structure| 5337-03-1
Chemical Structure| 5337-03-1
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Product Details of [ 5337-03-1 ]

CAS No. :5337-03-1 MDL No. :MFCD00031016
Formula : C6H10O3 Boiling Point : No data available
Linear Structure Formula :- InChI Key :AVPKHOTUOHDTLW-UHFFFAOYSA-N
M.W : 130.14 Pubchem ID :219302
Synonyms :

Calculated chemistry of [ 5337-03-1 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.83
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 31.7
TPSA : 46.53 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.02 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.2
Log Po/w (XLOGP3) : 0.1
Log Po/w (WLOGP) : 0.5
Log Po/w (MLOGP) : 0.0
Log Po/w (SILICOS-IT) : 0.78
Consensus Log Po/w : 0.52

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -0.64
Solubility : 29.5 mg/ml ; 0.227 mol/l
Class : Very soluble
Log S (Ali) : -0.63
Solubility : 30.4 mg/ml ; 0.233 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.11
Solubility : 100.0 mg/ml ; 0.769 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.81

Safety of [ 5337-03-1 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P305+P351+P338 UN#:
Hazard Statements:H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 5337-03-1 ]

* 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 [ 5337-03-1 ]

[ 5337-03-1 ] Synthesis Path-Downstream   1~8

  • 1
  • [ 5337-03-1 ]
  • [ 498-63-5 ]
  • (2-Hydroxymethyl-pyrrolidin-1-yl)-(tetrahydro-pyran-4-yl)-methanone [ No CAS ]
  • 2
  • [ 5337-03-1 ]
  • [ 6638-79-5 ]
  • [ 156353-01-4 ]
YieldReaction ConditionsOperation in experiment
96% With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine; In dichloromethane; water; at 0 - 20℃; for 2h; N,N- diisopropylethylamine (8.1 mL, 46 mmol) was slowly added to a cold (0 C) solution of tetrahydro-2H-pyran-4-carboxylic acid (2 g, 15 mmol) and O,N-Dimethyl-hydroxylamine hydrochloride (2.25 g, 23.05 mmol) in DCM (20 mL). To the above solution was added 2,4,6- tripropyl-1,3,5,2,4,6-trioxatriphosphinane 2,4,6-trioxide (11 mL, 50 %w/w; 18.4 mmol) slowly while at 0 C. The mixture was warmed to rt and allowed to stir for 2 h. The reaction mixture was quenched with ice cubes then diluted with water (10 mL) and extracted with DCM (2 X 30 mL). The organic fractions were combined, washed with aq. sodium bicaronate solution, dried (Na2SO4), filtered, and concentrated under reduced pressure to provide the title compound as an oily liquid (2.56 g, 96%). 1H NMR (400MHz, CD3OD) ^ = 3.96 (ddd, J = 1.7, 4.0, 11.5 Hz, 2H), 3.75 (s, 3H), 3.49 (dt, J = 2.4, 11.7 Hz, 2H), 3.19 (s, 3H), 3.10 - 2.92, (m, 1H), 1.83 - 1.60 (m, 4H); [M+H] = 174.2.
89% In a 1 L RB flask, a solution of tetrahydro-2H-pyran-4-carboxylic acid (46.0 g, 353 mmol) in dichloromethane (250 mL) was treated with 1,1?-carbonyldiimidazole (63.0 g, 389 mmol) portion-wise-caution bubbling. After the addition was complete the mixture was stirred at room temperature for 2 h and then treated portion wise with N,O-dimethylhydroxylamine, HCl (37.9 g, 389 mmol) and then stirred overnight at room temperature. Washed with water and brine, dried over MgSO4, filtered, and concentrated to give N-methoxy-N-methyloxane-4-carboxamide (55.0 g, 302 mmol, 85%) as light amber oil. 1H NMR (400 MHz, CDCl3) delta 4.02 (ddd, J=11.4, 4.2, 2.1 Hz, 2H), 3.71 (s, 3H), 3.46 (td, J=11.8, 2.2 Hz, 2H), 3.19 (s, 3H), 1.93-1.80 (m, 2H), 1.69-1.62 (m, 2H).
87% Tetrahydro-2H-pyran-4-carboxylic acid (13 g, 100 mmol) was dissolved in dichloromethane (200 mL), and cooled in an ice water bath. N,N-dimethyl formamide (0.1 mL) was added, and then oxalyl chloride (15.2 g, 120 mmol) was added dropwise slowly. After the dropwise addition was completed, the resulting mixture was stirred at 0C for additional 1h. The solvent was removed under vacuum to obtain an oily substance, which was dissolved in dichloromethane (100 mL). The resulting solution was added to a mixed solution of N,N-dimethylhydroxylamine hydrochloride (9.75 g, 100 mmol), diisopropyl ethylamine (39 g, 300 mmol) and dichloromethane (200 mL). The reaction mixture was stirred at room temperature overnight. The reaction mixture was poured into water, and extracted with ethyl acetate. The organic phase was washed with a saturated sodium chloride aqueous solution, and dried with anhydrous sodium sulfate. The solvent was removed under vacuum to obtain the product (15 g, 87%). 1H NMR (400 MHz, CDCl3): delta 4.00-4.05 (m, 2H), 3.72 (s, 3H), 3.44-3.50 (m, 2H), 3.20 (s, 3H), 2.89-2.95 (m, 1H), 1.82-1.92 (m, 2H), 1.64-1.68 (m, 2H).
81% With 4-methyl-morpholine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃; for 18h; [0239] To a solution of tetrahydro-2H-pyran-4-carboxylic acid 1 (4.0 g, 31 mmol) in DCM (65 mL) was added sequentiallyN,O-dimethylhydroxylamine hydrochloride (3.3 g, 34 mmol), 4-methylmorpholine (7.4 mL, 68 mmol), and N-(3-dimethylaminopropyl)-N?-ethylcarbodiimide hydrochloride (6.5 g, 34 mmol). The resulting mixture was stirred at RT for 18 h. Atthat time, the reaction was diluted with 1 N HCl and EtOAc and stirred vigorously until both phases cleared. The phases were separated, and the aqueous layer was extracted with EtOAc. The organic portions were combined, washed withbrine, dried over MgSO4, filtered, and concentrated. The crude residue was subjected to column chromatography (120g silica, 80 mL/min, 0% to 100% EtOAc/hexanes) to give N-methoxy-N-methyltetrahydro-2H-pyran-4-carboxamide 2(4.3 g, 24.8 mmol, 81%). LCMS for 2 (conditions D): tR = 1.12 min, m/e = 174.3 (M+H, base).
73.3% With 1,1'-carbonyldiimidazole; In dichloromethane; at 20℃; for 16h; The racemate of the methyl ester of the title compound was prepared according the literature using the scheme described above (US 2016/0176864). [00237] Methyl 3-(3,5-dimethylisoxazol-4-yl)-5-(phenyl(tetrahydro-2H-pyran-4-yl)methyl)- 5H-pyrido[3,2-b]indole-7-carboxylate (0.22 g, prepared according to literature and the synthetic route above) was separated by chiral HPLC to give (R)-methyl 3-(3,5- dimethylisoxazol-4-yl)-5-(phenyl(tetrahydro-2H-pyran-4-yl)methyl)-5H-pyrido[3,2-b]indole-7- carboxylate (0.095 g) and (S)-methyl 3-(3,5-dimethylisoxazol-4-yl)-5-(phenyl(tetrahydro-2H- pyran-4-yl)methyl)-5H-pyrido[3,2-b]indole-7-carboxylate (0.090 g) as a yellow solid. H NMR (racemate) (400 MHz, CDC13) delta 0.98-1.02 (IH, m), 1.32-1.36 (2H, m), 1.95 (IH, s), 2.15 (3H, s), 2.31 (3H, s), 3.00-3.08 (IH, m), 3.24-3.31 (IH, m), 3.45-3.51 (IH, m), 3.76-3.80 (IH, m), 3.96 (3H, s), 4.00-4.01 (IH, m), 5.52 (IH, d, J = 10.8 Hz), 7.22-7.29 (3H, m), 7.38-7.40 (2H, m), 7.51 (IH, d, J = 1.6 Hz), 7.99 (IH, dd, / = 8.0, 1.2 Hz), 8.36 (IH, d, J = 8.0 Hz), 8.39 (2H, s); LC/MS 496.3 [M+H]+. [00238] The chiral material ester was hydrolyzed under basic condition (aq. NaOH in MeOH) to provide (R)-PTM-3-l-A and (S)-PTM-3-l-B.
Add Iota, Gamma-carbonyldiimidazole (333.41 g, 1.2 eq) to a solution of tetrahydro-2H- pyran-4-carboxylic acid (223 g, 1.71 mol) in dichloromethane (2.23 L) portion wise over 15 minutes. Stir for two hours. Add Nu,Omicron-dimethylhydroxylamine hydrochloride (183.86 g, 1.1 eq) portionwise and stir for three hours. Wash the organics with saturated aqueous ammonium chloride, then with saturated aqueous sodium chloride. Dry the organics over anhydrous magnesium sulfate and concentrate in vacuo to give N-methoxy-N-methyl- tetrahydropyran-4-carboxamide (339 g, 1 14%) as crude material and use as such in next reaction. XH NMR (300 MHz, DMSO-d6) delta 4.02 (m, 2H), 3.71 (s, 3H), 3.46 (m, 2H), 3.19 (s, 3H), 2.91 (m, 1H), 1.86 (m, 2H), 1.65 (m, 2H).
831 mg With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In N,N-dimethyl-formamide; at 10 - 35℃; A) N-methoxy-N-methyltetrahydro-2H-pyran-4-carboxamide To a solution of tetrahydro-2H-pyran-4-carboxylic acid (800 mg) in N,N-dimethylformamide (60.0 mL) were added 1-hydroxybenzotriazole monohydrate (1.17 g), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.44 g), N,O-dimethylhydroxylamine hydrochloride (600 mg) and triethylamine (1.73 mL). The reaction mixture was stirred overnight at room temperature, water was added thereto, and the mixture was extracted with ethyl acetate. The extract was washed successively with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to give the title compound (831 mg). MS (API+): [M+H]+174.3.
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; at 20℃; Triethylamine (10.6 mL, 76.4 mmol) was added slowly to a mixture of tetrahydro-2H-pyran-4-carboxylic acid (4.97 g, 38.2 mmol), N,O-dimethylhydroxylamine hydrochloride (4.18 g, 42.0 mmol), and EDCI (8.79 g, 45.8 mmol) in DCM (48 mL). The white suspension was stirred at room temperature overnight. The mixture was diluted with saturated aqueous NaHCO3 and water and was stirred for 30 minutes. The phases were separated and the organic phase was washed with 1 N aqueous HCl followed by water. The organic phase was dried (Na2SO4), filtered, and concentrated to provide the title compound as a colorless oil.
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; at 20℃; Intermediate 1: step a Procedure A Triethylamine (10.6 mL, 76,4 mmol) was added slowly to a mixture of tetrahydro-2H-pyran-4- carboxylic acid (4.97 g, 38.2 mmol), N,0-dim.ethy3.hydroxylamine hydrochloride (4.18 g, 42.0 mmol), and EDO (8,79 g, 45.8 mmol) in DCM (48 mL). The white suspension was stirred at room temperature overnight. The mixture was diluted with saturated aqueous NaHC03and water and was stirred for 30 minutes. The phases were separated and the organic phase was washed with 1 N aqueous HC1 followed by water. The organic phase was dried (Na2S04), filtered, and concentrated to provide the title compound as a colorless oil.
To a solution of tetrahydro-2H-pyran-4-carboxylic acid (5.2 g, 39.9 mmol) in DCM (8.3 mL), CDI (7.12 g, 43.9 mmol) was added and the mixture was stirred for 45 minutes after which N,O-dimethylhydroxylamine hydrochloride (4.29 g, 43.9 mmol) was added and the mixture was stirred for 48 hours. The reaction mixture was quenched with 0.3 M aqueous solution of NaOH and partitioned between water and DCM. The aqueous layer was extracted with DCM, washed with aqueous saturated solution of NaCl, dried (MgSO4) and concentrated. The crude product was used without any further purification.

  • 3
  • [ 5337-03-1 ]
  • [ 141095-78-5 ]
  • 4
  • [ 5337-03-1 ]
  • Ν,Ο-dimethylhydroxylamine hydrochloride [ No CAS ]
  • [ 156353-01-4 ]
YieldReaction ConditionsOperation in experiment
89% Step 1: N-Methoxy-N-methyloxane-4-carboxamideTo a 500 mL round bottom flask containing a solution of oxane-4-carboxylic acid (8.00 g, 61.5 mmol) in CH2C12 (100 mL), 1,1?-carbonyldiimidazole (12.0 g, 73.8 mmol)was added in portions. The reaction solution was stirred at room temperature for 2 h. N,O-Dimethylhydroxylamine hydrochloride (6.60 g, 67.6 mmol) then was added in one portion. The reaction was stirred at room temperature for 16 h. The reaction mixture was quenched with saturated aq. ammonium chloride and separated. The organic layer was washed with saturated aq. NaHCO3, dried with sodium sulfate, filtered, and concentratedto give the title compound (9.50 g, 89 %), which was used as without purification. ?H NMR(400MHz, CD3OD)oe 3.99 (ddd,J11.5, 4.2, 2.1 Hz, 2H), 3.77 (s, 3H), 3.51 (td, J=1 1.8, 2.4 Hz, 2H), 1.7 Hz, 1H), 3.21 (s, 3H), 3.06 (br. s., 1H), 1.88-1.52 (m, 4H); LCMS (M+H) = 174.2; HPLC RT = 1.39 mm (Column: Waters Sunfire C18, 2.1 x 50mm, 3.5-tim particles; Mobile Phase A: 10:90 MeOH:water with 0.1% TFA; Mobile Phase B: 90:10 MeOH:water with 0.1% TFA; Temperature: 40C; Gradient: 0-100% B over 4 mm, then a 1.00 mm hold at 100% B; Flow: 4 mL/min; Detection: UV at 220 nm).
  • 5
  • [ 186581-53-3 ]
  • [ 5337-03-1 ]
  • [ 141095-78-5 ]
YieldReaction ConditionsOperation in experiment
[0220] To a stirred solution of tetrahydro-2H-pyran-4-carboxylic acid (1.5 g, 0.01 mmol) in CH2C12 (10 mL) was added oxalyl chloride (1.6 g, 0.01 mmol) and DMF (1 drop) at 0 C. The reaction mixture was warmed to RT and stirred for 2 h. After consumption of acid (monitored by TLC), the mixture was concentrated in vacuo. The crude mateiral was dissolved in ether and cooled to -10 C. A solution of CH2N2 in ether (20 mL) was added and the reaction mixture was warmed to RT and stirred for 19 h. After consumption of the starting materials (monitored by TLC), the mixture was concentrated in vacuo. To a stirred solution of the crude material in CH2C12 (20 mL) was added a solution of 48% aq HBr (5 mL) at -10 C. The reaction mixture was warmed to RT and stirred for 1 h. After consumption of the starting materials (monitored by TLC), the reaction was quenched with a sodium bicarbonate solution (50 mL) and extracted with CH2C12 (2 x 50 mL). The combined organic extracts were washed successively with a sodium bicarbonate solution (20 mL) and water (20 mL). The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo to afford 2-bromo-l-(tetrahydro-2H-pyran-4-yl) ethan-l-one (2 g, crude) as a yellow solid. 1H- NMR (DMSO- 500 MHz): delta 4.49 (s, 2H), 3.83 (d, 2H), 3.33 (t, 2H), 2.90-2.80 (m, 1H), 1.80-1.70 (m, 2H), 1.57-1.44 (m, 2H); TLC: 30% EtOAc:hexanes (Rf. 0.7).
2 g Synthesis of 2-bromo-1-(tetrahydro-2H-pyran-4-yl) ethan-1-one To a stirred solution of tetrahydro-2H-pyran-4-carboxylic acid (1.5 g, 0.01 mmol) in CH2Cl2 (10 mL) was added oxalyl chloride (1.6 g, 0.01 mmol) and DMF (1 drop) at 0 C. The reaction mixture was warmed to room temperature and stirred for 2 h. After consumption of acid (monitored by TLC), the mixture was concentrated in vacuo. The crude material was dissolved in ether and cooled to -10 C. A solution of CH2N2 in ether (20 mL) was added and the reaction mixture was warmed to room temperature and stirred for 16 h. After consumption of the starting material (monitored by TLC), the mixture was concentrated in vacuo. To a stirred solution of the crude material in CH2Cl2 (20 mL) was added a solution of 48% aq HBr (5 mL) at -10 C. The reaction mixture was warmed to room temperature and stirred for 1 h. After consumption of the starting material (monitored by TLC), the reaction was quenched with a sodium bicarbonate solution (50 mL) and extracted with CH2Cl2 (2*50 mL). The combined organic extracts were washed successively with a sodium bicarbonate solution (20 mL) and water (20 mL). The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo to afford 2-bromo-1-(tetrahydro-2H-pyran-4-yl) ethan-1-one (2 g) as a yellow solid. 1H-NMR (DMSO-d6, 500 MHz): delta 4.49 (s, 2H), 3.83 (d, 2H), 3.33 (t, 2H), 2.90-2.80 (m, 1H), 1.80-1.70 (m, 2H), 1.57-1.44 (m, 2H); TLC: 30% EtOAc:hexanes (Rf: 0.7).
  • 6
  • [ 5337-03-1 ]
  • [ 18107-18-1 ]
  • [ 141095-78-5 ]
YieldReaction ConditionsOperation in experiment
93.48% Method 1: (0047) Add oxalyl chloride (28.69 mL, 330.73 mmol) dropwise to a mixture of tetrahydropyran-4-carboxylic acid (39.13 g, 300.67 mmol) in DCM (250 mL) and DMF (15 drops). Stir the mixture at room temperature for 2.5 hours under nitrogen. Concentrate under reduced pressure and dissolve the residue in DCM (250 mL). Add the resulting solution dropwise to (trimethylsilyl)diazomethane (2M in hexanes, 450 mL, 900.00 mmol) at -10 C. and stir the mixture at room temperature overnight. Cool the mixture to 0 C. and add hydrobromic acid (48 wt/wt % in water, 52 mL, 462.73 mmol) dropwise. Stir the mixture at room temperature for two hours. Cool the mixture to 0 C. and add hydrobromic acid (48 wt/wt % in water, 26 mL, 231.36 mmol) dropwise. Stir the mixture at room temperature for two hours. Add water (250 mL), DCM (250 mL) and isolate the organic layer. Extract the aqueous layer with DCM (2×250 mL). Combine the organic layers and wash with saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride. Dry over anhydrous sodium sulfate and concentrate under reduced pressure to give the title compound (58.2 g; 93.48% yield) as a brown solid. 1H NMR (300 MHz, CDCl3) delta 4.00 (m, 2H), 3.95 (s, 2H), 3.45 (m, 2H), 2.98 (m, 1H), 1.78 (m, 4H).
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