Thionyl Chloride → HCID 12109145, compound

HRID 641159Notes

Reaction equation

HRID 641159 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([C:14]1[CH:22]=[CH:21][C:17]([C:18](O)=[O:19])=[CH:16][CH:15]=1)[CH3:13])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)([Cl:25])=O>ClCCl.CN(C)C=O>[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([C:14]1[CH:22]=[CH:21][C:17]([C:18]([Cl:25])=[O:19])=[CH:16][CH:15]=1)[CH3:13])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=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

To a solution of (R)-4-(1-benzyloxycarbonylaminoethyl)-benzoic acid (1.2 g) in dichloromethane (15 mL) were added thionyl chloride (0.9 mL) and one drop of dimethylformamide, and the mixture was stirred at room temperature for 2 hrs. After the reaction, the solvent was evaporated under reduced pressure to give (R)-4-(1-benzyloxycarbonylaminoethyl)benzoic acid chloride as crystals. Then, the crystals were dissolved in acetonitrile (10 mL) and added dropwise to a solution of 4-amino-1H-pyrrolo[2,3-b]pyridine (240 mg) and diisopropylethylamine (520 mg) in acetonitrile (10 mL), and the mixture was stirred at room-temperature for 8 hrs. The precipitated crystals were collected by filtration, dried and dissolved in methanol (7 mL). Sodium methoxide (60 mg) was added and the mixture was stirred at room temperature for 30 min. After the reaction, the mixture was concentrated under reduced pressure. Water was added to the obtained residue and the mixture was extracted with ethyl acetate. The extract was dried and the solvent was evaporated under reduced pressure. The obtained crystals were washed with ethyl acetate to give (R)—N-(1H-pyrrolo[2,3-b]pyridin-4-yl)-4-(1-benzyloxycarbonylaminoethyl)benzamide (330 mg).

Workup

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

Sources & evidence

ORD record
ord-5ad9a375c99e4c3da730bcb4d932cf21
Source dataset
uspto-grants-2010_04
Patent number
US07696194B2

Reaction notes

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