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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 61673
Notes
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Reaction equation

HRID 61673 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 761712-chloro-N-(1-methylethyl)acetamideHCID 59361970tert-Butyl 5-(2-(3-hydroxyphenyl)-7-methoxy-6-(2-methoxyethoxy)quinazolin-4-ylamino)-1H-indazole-1-carboxylate

Product 1

HCID 59361834tert-butyl 5-(2-(3-(2-(isopropylamino)-2-oxoethoxy)phenyl)-7-methoxy-6-(2-methoxyethoxy)quinazolin-4-ylamino)-1H-indazole-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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

  1. concentrationThe mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-ac9004650c9346899e389dabcad299df
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