2-(6-{[(Ethylamino)carbonyl]amino}pyridin-3-yl)-N-(1-methyl-1-phenylethyl)-1,3-thiazole-5-carboxamide → 2-(6-{[(Ethylamino)carbonyl]amino}pyridin-3-yl)-1,3-thiazole-5-carboxamide
Reaction equation
[CH2:1]([NH:3][C:4]([NH:6][C:7]1[N:12]=[CH:11][C:10]([C:13]2[S:14][C:15]([C:18]([NH:20]C(C)(C3C=CC=CC=3)C)=[O:19])=[CH:16][N:17]=2)=[CH:9][CH:8]=1)=[O:5])[CH3:2]>C(O)(C(F)(F)F)=O>[CH2:1]([NH:3][C:4]([NH:6][C:7]1[N:12]=[CH:11][C:10]([C:13]2[S:14][C:15]([C:18]([NH2:20])=[O:19])=[CH:16][N:17]=2)=[CH:9][CH:8]=1)=[O:5])[CH3:2]Participants
3
Procedure
2-(6-{[(Ethylamino)carbonyl]amino}pyridin-3-yl)-N-(1-methyl-1-phenylethyl)-1,3-thiazole-5-carboxamide (Intermediate 18, 53 mg, 0.129 mmol) was dissolved in TFA (1 mL) and the solution was stirred overnight. TFA was removed under reduced pressure and the crude was partitioned between aqueous sodium bicarbonate and EtOAc. The layers separated and the organic layer was washed with water and brine. During the work up process the product precipitated which was collected by filtration. Washed with water and EtOAc and dried (0.020 g). MS (ESP): 292 (M+H+) for C12H13N5O2S; NMR: 1.09 (t, 3H), 3.16-3.22 (m, 2H), 7.56 (d, 1H), 7.65 (brs, 1H), 7.83 (brs, 1H), 8.15-8.23 (m, 2H), 8.40 (s, 1H), 8.77 (s, 1H), 9.51 (s, 1H).
Workup
- customTFA was removed under reduced pressure
- customthe crude was partitioned between aqueous sodium bicarbonate and EtOAc
- customThe layers separated
- washthe organic layer was washed with water and brine
- customDuring the work up process the product precipitated which
- filtrationwas collected by filtration
- washWashed with water and EtOAc
- customdried (0.020 g)
Sources & evidence
- ORD record
- ord-9d5d3b755c6745af90f635c1c856786e
- Source dataset
- uspto-grants-2010_03
- Patent number
- US07674801B2
Reaction notes
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