Nitrogen → tert-Butyl 5-(2-(3-hydroxyphenyl)-7-methoxy-6-(2-methoxyethoxy)quinazolin-4-ylamino)-1H-indazole-1-carboxylate

HRID 1407022Notes

Reaction equation

HRID 1407022 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([C:15]2[N:24]=[C:23]([NH:25][C:26]3[CH:27]=[C:28]4[C:32](=[CH:33][CH:34]=3)[N:31]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[N:30]=[CH:29]4)[C:22]3[C:17](=[CH:18][C:19]([O:47][CH3:48])=[C:20]([O:42][CH2:43][CH2:44][O:45][CH3:46])[CH:21]=3)[N:16]=2)[CH:12]=[CH:13][CH:14]=1)C1C=CC=CC=1.N#N>CO.COCCOC.[Pd]>[OH:8][C:9]1[CH:10]=[C:11]([C:15]2[N:24]=[C:23]([NH:25][C:26]3[CH:27]=[C:28]4[C:32](=[CH:33][CH:34]=3)[N:31]([C:35]([O:37][C:38]([CH3:40])([CH3:41])[CH3:39])=[O:36])[N:30]=[CH:29]4)[C:22]3[C:17](=[CH:18][C:19]([O:47][CH3:48])=[C:20]([O:42][CH2:43][CH2:44][O:45][CH3:46])[CH:21]=3)[N:16]=2)[CH:12]=[CH:13][CH:14]=1

Participants

6

Reactant 2

HCID 947NitrogenHCID 59361896tert-butyl 5-(2-(3-(benzyloxy)phenyl)-7-methoxy-6-(2-methoxyethoxy)quinazolin-4-ylamino)-1H-indazole-1-carboxylate

Product 1

HCID 59361970tert-Butyl 5-(2-(3-hydroxyphenyl)-7-methoxy-6-(2-methoxyethoxy)quinazolin-4-ylamino)-1H-indazole-1-carboxylateYield 97%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

A suspension of tert-butyl 5-(2-(3-(benzyloxy)phenyl)-7-methoxy-6-(2-methoxyethoxy)quinazolin-4-ylamino)-1H-indazole-1-carboxylate (2.70 g, 4.17 mmol) in MeOH (400 mL) and DME (200 mL) was added Pd/C (10%, wet, 0.500 g) under an atmosphere of N2. The N2 was exchanged for H2 and the mixture was stirred under an atmosphere of H2 (balloon pressure) overnight. The mixture was filtered through a pad of Celite® and the filtrate was concentrated in vacuo to give tert-Butyl 5-(2-(3-hydroxyphenyl)-7-methoxy-6-(2-methoxyethoxy)quinazolin-4-ylamino)-1H-indazole-1-carboxylate (2.25 g, 4.04 mmol, 97%). MS 558 (M+1). HPLC retention time 6.44 mins.

Workup

  1. filtrationThe mixture was filtered through a pad of Celite®
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-bdee011b82ab46d8a203eb366df38020
Source dataset
uspto-grants-2014_12
Patent number
US08916576B2

Reaction notes

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