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1,1-Dimethylethyl 5-amino-1H-indazole-1-carboxylate → tert-butyl 5-(2-(3-acetoxyphenyl)quinazolin-4-ylamino)-1H-indazole-1-carboxylate

HRID 61531
Notes
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Reaction equation

HRID 61531 reaction equation
[C:1]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]2[N:20]=[C:19](Cl)[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[N:12]=2)[CH:6]=1)(=[O:3])[CH3:2].[NH2:22][C:23]1[CH:24]=[C:25]2[C:29](=[CH:30][CH:31]=1)[N:28]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[N:27]=[CH:26]2>C(O)(C)C>[C:1]([O:4][C:5]1[CH:6]=[C:7]([C:11]2[N:20]=[C:19]([NH:22][C:23]3[CH:24]=[C:25]4[C:29](=[CH:30][CH:31]=3)[N:28]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[N:27]=[CH:26]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:3])[CH3:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 198005561,1-Dimethylethyl 5-amino-1H-indazole-1-carboxylateHCID 593619303-(4-Chloroquinazolin-2-yl)phenyl acetate

Product 1

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

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
95 °C

Procedure

3-(4-Chloroquinazolin-2-yl)phenyl acetate (9.77 g, 29.97 mmole) was dissolved in isopropanol (290 mL) and tert-butyl 5-amino-1H-indazole-1-carboxylate (6.99 g, 29.97 mmole) was added. The solution was heated to 95° C. and stirred for 0.25 h. A gelatinous formation developed which was manually broken up and dissolution gradually occurred followed by formation of a yellow precipitate. The reaction was stirred for an additional 0.25 h, cooled to ambient temperature and filtered. The filtered solid was washed with ether and then dried under high vacuum overnight to give tert-butyl 5-(2-(3-acetoxyphenyl)quinazolin-4-ylamino)-1H-indazole-1-carboxylate. (14.58 g, mmol, 98%)

Workup

  1. dissolutiondissolution
  2. stirringThe reaction was stirred for an additional 0.25 h
  3. temperaturecooled to ambient temperature
  4. filtrationfiltered
  5. washThe filtered solid was washed with ether
  6. customdried under high vacuum overnight

Sources & evidence

ORD record
ord-ec1a78e88d69463897e1d5ae76f07256
Source dataset
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09440961B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes