Ammonium Hydroxide → 1H-Indazole-1-carboxylic acid, 5-[[2-(3-hydroxyphenyl)-4-quinazolinyl]amino]-, 1,1-dimethylethyl ester

HRID 61532Notes

Reaction equation

HRID 61532 reaction equation
C([O:4][C:5]1[CH:6]=[C:7]([C:11]2[N:20]=[C:19]([NH:21][C:22]3[CH:23]=[C:24]4[C:28](=[CH:29][CH:30]=3)[N:27]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[N:26]=[CH:25]4)[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[N:12]=2)[CH:8]=[CH:9][CH:10]=1)(=O)C.[NH4+].[OH-]>CO>[OH:4][C:5]1[CH:6]=[C:7]([C:11]2[N:20]=[C:19]([NH:21][C:22]3[CH:23]=[C:24]4[C:28](=[CH:29][CH:30]=3)[N:27]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[N:26]=[CH:25]4)[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[N:12]=2)[CH:8]=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 66826370tert-butyl 5-(2-(3-acetoxyphenyl)quinazolin-4-ylamino)-1H-indazole-1-carboxylate

Product 1

HCID 569494541H-Indazole-1-carboxylic acid, 5-[[2-(3-hydroxyphenyl)-4-quinazolinyl]amino]-, 1,1-dimethylethyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of give tert-butyl 5-(2-(3-acetoxyphenyl)quinazolin-4-ylamino)-1H-indazole-1-carboxylate (5.85 g, 11.8 mmole) in anhydrous MeOH (400 mL) was added 28% (wt/v) NH4OH solution (6.50 mL). The reaction mixture was stirred at ambient temperature for 48 h. The crude product was filtered and washed with ether followed by hexane and dried under high vacuum overnight to give tert-butyl 5-(2-(3-hydroxyphenyl)-quinazolin-4-ylamino)-1H-indazole-1-carboxylate. (4.85 g, mmol, 91%).

Workup

  1. filtrationThe crude product was filtered
  2. washwashed with ether
  3. customdried under high vacuum overnight

Sources & evidence

ORD record
ord-1519c93e7cd948a8aae13cebfae2b710
Source dataset
uspto-grants-2016_09
Patent number
US09440961B2

Reaction notes

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