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

HRID 61535Notes

Reaction equation

HRID 61535 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2[N:19]=[C:18]([NH:20][C:21]3[CH:22]=[C:23]4[C:27](=[CH:28][CH:29]=3)[N:26]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[N:25]=[CH:24]4)[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11]=2)[CH:7]=[CH:8][CH:9]=1)([O-])=O.[H][H]>COCCOC.CO.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]([C:10]2[N:19]=[C:18]([NH:20][C:21]3[CH:22]=[C:23]4[C:27](=[CH:28][CH:29]=3)[N:26]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[N:25]=[CH:24]4)[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11]=2)[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 66826553tert-butyl 5-(2-(3-nitrophenyl)quinazolin-4-ylamino)-1H-indazole-1-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 66825994tert-butyl 5-(2-(3-aminophenyl)quinazolin-4-ylamino)-1H-indazole-1-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 86595564Dimethoxyethane methanolSolvent

Procedure

A suspension of product tert-butyl 5-(2-(3-nitrophenyl)quinazolin-4-ylamino)-1H-indazole-1-carboxylate (9.0 g, 18.65 mmole) in a mixture of DME/MeOH (300 mL/100 mL) was hydrogenated in the presence of 10% Pd/C (1.25 g) at RT using a balloon filled with hydrogen gas. The reaction was stirred for 16 h and the reaction mixture filtered through Celite™. The pad of Celite™ was washed with a 1:1 mixture of MeOH/CH2Cl2 (200 mL). The filtrate was then concentrated in vacuo and dried under high vacuum overnight to give tert-butyl 5-(2-(3-aminophenyl)quinazolin-4-ylamino)-1H-indazole-1-carboxylate. (8.8 g, mmol, %).

Workup

  1. filtrationthe reaction mixture filtered through Celite™
  2. washThe pad of Celite™ was washed with a 1:1 mixture of MeOH/CH2Cl2 (200 mL)
  3. concentrationThe filtrate was then concentrated in vacuo
  4. customdried under high vacuum overnight

Sources & evidence

ORD record
ord-3703fbd5c36749ecab97ad67029f341f
Source dataset
uspto-grants-2016_09
Patent number
US09440961B2

Reaction notes

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