Water → HCID 178489402, compound

HRID 1865635Notes

Reaction equation

HRID 1865635 reaction equation
[Br:1][CH2:2][C:3]([NH:5][C:6]1[CH:16]=[CH:15][C:14]([C:17]2[CH:18]=[C:19]3[C:25]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=4[O:32][CH3:33])=[N:24][N:23](COCC[Si](C)(C)C)[C:20]3=[N:21][CH:22]=2)=[CH:13][C:7]=1[C:8]([N:10]([CH3:12])[CH3:11])=[O:9])=[O:4].Cl(O)(=O)(=O)=O.O>C(O)(=O)C>[Br:1][CH2:2][C:3]([NH:5][C:6]1[CH:16]=[CH:15][C:14]([C:17]2[CH:18]=[C:19]3[C:25]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=4[O:32][CH3:33])=[N:24][NH:23][C:20]3=[N:21][CH:22]=2)=[CH:13][C:7]=1[C:8]([N:10]([CH3:12])[CH3:11])=[O:9])=[O:4]

Participants

5

Reactant 3

HCID 962WaterHCID 24247Perchloric AcidHCID 579758972-(2-bromo-acetylamino)-5-[3-(2-methoxy-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-N,N-dimethyl-benzamide

Product 1

HCID 178489402HCID 178489402, compoundYield 68.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

300 mg of 2-(2-bromo-acetylamino)-5-[3-(2-methoxy-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-N,N-dimethyl-benzamide was dissolved in 5 mL of glacial acetic acid. 400 μL of 70% perchloric acid was added and the resulting solution stirred at ambient temperature for 23 h. 85 mL of water was added and the resulting precipitate filtered off and dried by suction to afford 162 mg (0.32 mmol, 68%) of 2-(2-bromo-acetylamino)-5-[3-(2-methoxy-phenyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-N,N-dimethyl-benzamide as a yellow solid. MS: m/z 508.0+510.1 (M+H+).

Workup

  1. filtrationthe resulting precipitate filtered off
  2. customdried by suction

Sources & evidence

ORD record
ord-326ae3a5a3bc42c5b0ec9f9248dd72ff
Source dataset
uspto-grants-2009_12
Patent number
US07626021B2

Reaction notes

Loading…