Water → HCID 178489402, compound

HRID 2388972Notes

Reaction equation

HRID 2388972 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-3bbc6d8b3ae74d6e87ce5cc14c0c76ed
Source dataset
uspto-grants-2012_09
Patent number
US08268994B2

Reaction notes

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