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

HRID 1808466Notes

Reaction equation

HRID 1808466 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][CH:12]=[CH:13][CH:14]=3)[N:9]=2)[CH:5]=[CH:6][CH:7]=1.[CH:35]([NH:38][C:39](=[O:42])[CH2:40]Br)([CH3:37])[CH3:36].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH:35]([NH:38][C:39](=[O:42])[CH2:40][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]([CH3:34])([CH3:33])[CH3:32])=[O:29])[N:23]=[CH:22]4)[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[N:9]=2)[CH:5]=[CH:6][CH:7]=1)([CH3:37])[CH3:36]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 125092612-Bromo-N-isopropylacetamideHCID 569494541H-Indazole-1-carboxylic acid, 5-[[2-(3-hydroxyphenyl)-4-quinazolinyl]amino]-, 1,1-dimethylethyl ester

Product 1

HCID 66826312tert-butyl 5-(2-(3-(2-(isopropylamino)-2-oxoethoxy)-phenyl)quinazolin-4-ylamino)-1H-indazole-1-carboxylateYield 45%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of tert-butyl 5-(2-(3-hydroxyphenyl)quinazolin-4-ylamino)-1H-indazole-1-carboxylate (0.3 g, 0.66 mmol), N-isopropylbromoacetamide (0.132 g, 0.726 mmole), and K2CO3 (0.183 g, 1.32 mmole) in DMF (3.6 mL) was heated overnight at 30° C. The crude product was poured onto ice-water (ca. 50 mL) and the suspension was stirred for approximately 0.5 h, filtered and dried (Na2SO4). The crude product was recrystallized from absolute EtOH (10 mL) to afford tert-butyl 5-(2-(3-(2-(isopropylamino)-2-oxoethoxy)-phenyl)quinazolin-4-ylamino)-1H-indazole-1-carboxylate (0.160 g, mmol, 45%).

Workup

  1. filtrationfiltered
  2. dry with materialdried (Na2SO4)
  3. customThe crude product was recrystallized from absolute EtOH (10 mL)

Sources & evidence

ORD record
ord-5448349eb0434a9ab8d1dd42541defd7
Source dataset
uspto-grants-2013_01
Patent number
US08357693B2

Reaction notes

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