Potassium Carbonate → tert-butyl 5-(2-(3-(2-(isopropylamino)-2-oxoethoxy)phenyl)-7-methoxy-6-(2-methoxyethoxy)quinazolin-4-ylamino)-1H-indazole-1-carboxylate

HRID 1407023Notes

Reaction equation

[OH:1][C:2]1[CH:3]=[C:4]([C:8]2[N:17]=[C:16]([NH:18][C:19]3[CH:20]=[C:21]4[C:25](=[CH:26][CH:27]=3)[N:24]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[N:23]=[CH:22]4)[C:15]3[C:10](=[CH:11][C:12]([O:40][CH3:41])=[C:13]([O:35][CH2:36][CH2:37][O:38][CH3:39])[CH:14]=3)[N:9]=2)[CH:5]=[CH:6][CH:7]=1.Cl[CH2:43][C:44]([NH:46][CH:47]([CH3:49])[CH3:48])=[O:45].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH:47]([NH:46][C:44](=[O:45])[CH2:43][O:1][C:2]1[CH:3]=[C:4]([C:8]2[N:17]=[C:16]([NH:18][C:19]3[CH:20]=[C:21]4[C:25](=[CH:26][CH:27]=3)[N:24]([C:28]([O:30][C:31]([CH3:33])([CH3:34])[CH3:32])=[O:29])[N:23]=[CH:22]4)[C:15]3[C:10](=[CH:11][C:12]([O:40][CH3:41])=[C:13]([O:35][CH2:36][CH2:37][O:38][CH3:39])[CH:14]=3)[N:9]=2)[CH:5]=[CH:6][CH:7]=1)([CH3:49])[CH3:48]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of tert-Butyl 5-(2-(3-hydroxyphenyl)-7-methoxy-6-(2-methoxyethoxy)quinazolin-4-ylamino)-1H-indazole-1-carboxylate (0.400 g, 0.72 mmol) and 2-chloro-N-isopropylacetamide (0.107 g, 0.79 mmol) in DMF (16 mL) was added K2CO3 (0.297 g, 1.44 mmol). The mixture was heated at 80° C. for 72 h. The mixture was concentrated in vacuo and taken on directly into the next step. HPLC retention time 6.76 mins.

Workup

concentrationThe mixture was concentrated in vacuo

Sources & evidence

ORD record: ord-59b660e58a254849bb3bb4e819d9f6ae
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08916576B2

Reaction notes

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