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

HRID 1406885
Notes
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Reaction equation

HRID 1406885 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[CH:13]=2)[N:3]=1.[NH2:21][C:22]1[CH:23]=[C:24]2[C:28](=[CH:29][CH:30]=1)[N:27]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[N:26]=[CH:25]2>C(O)(C)C>[N+:18]([C:14]1[CH:13]=[C:12]([C:4]2[N:3]=[C:2]([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:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]=2)[CH:17]=[CH:16][CH:15]=1)([O-:20])=[O:19]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 198005561,1-Dimethylethyl 5-amino-1H-indazole-1-carboxylateHCID 593619944-Chloro-2-(3-nitrophenyl)quinazoline

Product 1

HCID 66826553tert-butyl 5-(2-(3-nitrophenyl)quinazolin-4-ylamino)-1H-indazole-1-carboxylate

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
95 °C

Procedure

A suspension of 4-chloro-2-(3-nitrophenyl)quinazoline (6.3 g, 21.9 mmole), tert-butyl 5-amino-1H-indazole-1-carboxylate (5.10 g, 21.9 mmole) in isopropanol (300 mL) was heated at 95° C. for 1.5 h. The suspension was filtered and the filtered solid was washed with isopropanol. The product was dried under high vacuum for several hours to give the desired product tert-butyl 5-(2-(3-nitrophenyl)quinazolin-4-ylamino)-1H-indazole-1-carboxylate. (8.3 g, mmol, 79%).

Workup

  1. filtrationThe suspension was filtered
  2. washthe filtered solid was washed with isopropanol
  3. customThe product was dried under high vacuum for several hours

Sources & evidence

ORD record
ord-876c5c45b2b640c49b23d69a8f9519c6
Source dataset
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08916576B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes