Potassium Carbonate → HCID 23633225, compound

HRID 1158762Notes

Reaction equation

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

Participants

Conditions

Temperature: 75 °C

Procedure

2-Methoxy-1,1-dimethylethyl 4-[(bromoacetyl)amino]-2-(dimethylamino)-1-phenyl-1H-imidazole-5-carboxylate (35 mg, 1 eq, synthesized in an analogous manner/method as described for example 90), 2-indolinone (26 mg, 2.5 eq) and K2CO3 (22 mg, 2 eq) were dissolved in DMF (5 mL). The reaction was stirred for 1 h at 75° C. The solvent was evaporated off and to the residue was added K2CO3(aq) (1 M, 50 mL) and extracted with ether. The organic phases were pooled, dried (MgSO4.H2O), filtered and evaporated. Eventually the crude material was purified by preparatory HPLC, which gave pure product.

Workup

customThe solvent was evaporated off and to the residue
additionwas added K2CO3(aq) (1 M, 50 mL)
extractionextracted with ether
dry with materialdried (MgSO4.H2O)
filtrationfiltered
customevaporated
customEventually the crude material was purified by preparatory HPLC, which
customgave pure product

Sources & evidence

ORD record: ord-aeb4b13fa9b449569eab4d4bc0e22275
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07812026B2

Reaction notes

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