Thionyl Chloride → HCID 12109145, compound

HRID 619263Notes

Reaction equation

HRID 619263 reaction equation
S(Cl)([Cl:3])=O.[CH2:5]([O:12][C:13]([NH:15][C@@H:16]([C:18]1[CH:26]=[CH:25][C:21]([C:22](O)=[O:23])=[CH:20][CH:19]=1)[CH3:17])=[O:14])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>CN(C)C=O.ClCCl>[CH2:5]([O:12][C:13]([NH:15][C@@H:16]([C:18]1[CH:26]=[CH:25][C:21]([C:22]([Cl:3])=[O:23])=[CH:20][CH:19]=1)[CH3:17])=[O:14])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 12109144HCID 12109144, compound

Product 1

HCID 12109145HCID 12109145, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

Thionyl chloride (2 ml) and dimethylformamide (1 drop) were added to a solution of (R)-4-(1-benzyloxycarbonylaminoethyl)benzoic acid (1.11 g) in dichloromethane (10 ml), and the mixture was stirred at room temperature for 2 hours. After the reaction, the solvent was evaporated under reduced pressure to give (R)-4-(1-benzyloxycarbonylaminoethyl)benzoyl chloride as crystals. Then, the crystals were dissolved in acetonitrile (10 ml), and the solution was dropwise added to a mixed-solution of 4-amino-1H-pyrazolo[3,4-b]pyridine dihydrochloride (320 mg) and diisopropylethylamine (880 mg) in acetonitrile (10 ml)-dimethylimidazolidinone (3 ml). The mixture was stirred at room temperature for 5 hours. The precipitated crystals were collected by filtration and dried. The residue was dissolved in methanol (7 ml). Sodium methoxide (80 mg) was added, and the mixture was stirred at room temperature for 30 minutes. After the reaction, the mixture was concentrated under reduced pressure, and water was added to the obtained residue. The mixture was extracted with ethyl acetate and dried. The solvent was evaporated under reduced pressure, and the obtained crystals were washed with ethyl acetate to give 310 mg of (R)-N-(1H-pyrazolo[3,4-b]pyridin-4-yl)-4-(1-benzyloxycarbonylaminoethyl)benzamide.

Workup

  1. customAfter the reaction
  2. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-27974f3eb3c84974ae001ac1f9bd9c05
Source dataset
uspto-grants-1999_09
Patent number
US05958944

Reaction notes

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