Ammonia methanol → 5-(4-Fluorobenzamido)-2-[methyl(quinolin-6-yl)amino]thiazole-4-carboxamide

HRID 512545Notes

Reaction equation

[F:1][C:2]1[CH:32]=[CH:31][C:5]([C:6]([NH:8][C:9]2[S:13][C:12]([N:14]([CH3:25])[C:15]3[CH:16]=[C:17]4[C:22](=[CH:23][CH:24]=3)[N:21]=[CH:20][CH:19]=[CH:18]4)=[N:11][C:10]=2[C:26]([O:28]CC)=O)=[O:7])=[CH:4][CH:3]=1.[NH3:33].CO>C1COCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([NH:8][C:9]2[S:13][C:12]([N:14]([CH3:25])[C:15]3[CH:16]=[C:17]4[C:22](=[CH:23][CH:24]=3)[N:21]=[CH:20][CH:19]=[CH:18]4)=[N:11][C:10]=2[C:26]([NH2:33])=[O:28])=[O:7])=[CH:31][CH:32]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of ethyl 5-(4-fluorobenzamido)-2-[methyl(quinolin-6-yl)-amino]thiazole-4-carboxylate (0.14 g, 0.31 mmol) in THF (5 mL) was added 7N NH3-MeOH (5mL), and the mixture was heated at 80° C. for 16 hrs in a sealed tube. The solvent was evaporated in vacuo, and the resulting solids were purified by silica gel chromatography eluted with EtOAc to give 110 mg (84% yield) of the titled compound.

Workup

customThe solvent was evaporated in vacuo
customthe resulting solids were purified by silica gel chromatography
washeluted with EtOAc

Sources & evidence

ORD record: ord-95a603b1c49a49549cfc07e4d6da6256
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09102637B2

Reaction notes

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