Water → HCID 54150500, compound

HRID 1604593Notes

Reaction equation

Br[CH2:2][CH2:3][CH2:4][C:5]([NH:7][C:8]1[CH:44]=[CH:43][C:11]([CH:12]=[CH:13][C:14]([NH:16][CH2:17][C:18]([N:20]([C:22]2[C:23]([Cl:42])=[C:24]([C:38]([Cl:41])=[CH:39][CH:40]=2)[CH2:25][O:26][C:27]2[CH:28]=[CH:29][CH:30]=[C:31]3[C:36]=2[N:35]=[C:34]([CH3:37])[CH:33]=[CH:32]3)[CH3:21])=[O:19])=[O:15])=[CH:10][C:9]=1[CH3:45])=[O:6].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[Cl:42][C:23]1[C:22]([N:20]([CH3:21])[C:18](=[O:19])[CH2:17][NH:16][C:14](=[O:15])[CH:13]=[CH:12][C:11]2[CH:43]=[CH:44][C:8]([N:7]3[CH2:2][CH2:3][CH2:4][C:5]3=[O:6])=[C:9]([CH3:45])[CH:10]=2)=[CH:40][CH:39]=[C:38]([Cl:41])[C:24]=1[CH2:25][O:26][C:27]1[CH:28]=[CH:29][CH:30]=[C:31]2[C:36]=1[N:35]=[C:34]([CH3:37])[CH:33]=[CH:32]2

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 8-[3-[N-[4-(4-bromobutyramido)-3-methylcinnamoylglycyl]-N-methylamino]-2,6-dichlorobenzyloxy]-2-methylquinoline (110 mg) in N,N-dimethylformamide was added potassium carbonate (64 mg) and the mixture was stirred for 2 hours at 50° C. The mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with water and brine, dried and concentrated in vacuo. The residue was purified by preparative thin-layer chromatography (dichloromethane-methanol) to give 8-[2,6-dichloro-3-[N-methyl-N-[3-methyl-4-(2-oxopyrrolidin-1-yl)cinnamoylglycyl]amino]benzyloxy]-2-methylquinoline (72 mg) as an amorphous powder.

Workup

extractionextracted with ethyl acetate
washThe organic layer was washed with water and brine
customdried
concentrationconcentrated in vacuo
customThe residue was purified by preparative thin-layer chromatography (dichloromethane-methanol)

Sources & evidence

ORD record: ord-ecd769a819ec4721924f2ac588f89e79
Source dataset: uspto-grants-1999_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05994368

Reaction notes

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