Benzoyl chloride → HCID 59513854, compound

HRID 1159948Notes

Reaction equation

HRID 1159948 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[C:18]([C:19]3[CH:24]=[CH:23][N:22]=[CH:21][N:20]=3)=[C:11]3[CH:12]=[C:13]([CH2:16][OH:17])[CH:14]=[CH:15][N:10]3[N:9]=2)[CH:5]=[CH:6][CH:7]=1.[C:25](Cl)(=[O:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C(Cl)Cl>[OH:17][CH2:16][C:13]1[CH:14]=[CH:15][N:10]2[N:9]=[C:8]([C:4]3[CH:3]=[C:2]([NH:1][C:25](=[O:32])[C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[CH:7]=[CH:6][CH:5]=3)[C:18]([C:19]3[CH:24]=[CH:23][N:22]=[CH:21][N:20]=3)=[C:11]2[CH:12]=1

Participants

4

Reactant 2

HCID 7412Benzoyl chlorideHCID 59513688HCID 59513688, compound

Product 1

HCID 59513854HCID 59513854, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of [2-(3-aminophenyl)-3-(4-pyrimidinyl)pyrazolo[1,5-a]pyridin-5-yl]methanol (600 mg, 1.90 mmol) in DCM (60 mL), benzoyl chloride (0.440 mL, 3.79 mmol) was added dropwise at rt. The mixture was stirred for overnight. The reaction mixture was quenched to add MeOH, then the solvent was evaporated under reduced pressure. The residue was recrystallized from DCM (excess) and small amount of acetone. The title compound was obtained as yellow solid (820 mg).

Workup

  1. additionwas added dropwise at rt
  2. customThe reaction mixture was quenched
  3. additionto add MeOH
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was recrystallized from DCM (excess) and small amount of acetone

Sources & evidence

ORD record
ord-5b55ee6eb8b245a4b84a3e37d814b612
Source dataset
uspto-grants-2010_10
Patent number
US07812022B2

Reaction notes

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