Ethanol → (S)-6-(6-(3-ethylureido)-4-(4-(trifluoromethyl)thiazol-2-yl)pyridin-3-yl)-1-(1-hydroxy-4-methylpentan-2-yl)-N-methyl-4-oxo-1,4-dihydroquinoline-3-carboxamide

HRID 2061808Notes

Reaction equation

HRID 2061808 reaction equation
[CH2:1]([NH:3][C:4](=[O:44])[NH:5][C:6]1[N:11]=[CH:10][C:9]([C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[N:18]([C@@H:22]([CH2:25][CH:26]([CH3:28])[CH3:27])[CH2:23][OH:24])[CH:17]=[C:16]([C:29]([O:31]CC)=O)[C:15]3=[O:34])=[C:8]([C:35]2[S:36][CH:37]=[C:38]([C:40]([F:43])([F:42])[F:41])[N:39]=2)[CH:7]=1)[CH3:2].[CH3:45][NH2:46].C(O)C>>[CH2:1]([NH:3][C:4](=[O:44])[NH:5][C:6]1[N:11]=[CH:10][C:9]([C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[N:18]([C@@H:22]([CH2:25][CH:26]([CH3:27])[CH3:28])[CH2:23][OH:24])[CH:17]=[C:16]([C:29]([NH:46][CH3:45])=[O:31])[C:15]3=[O:34])=[C:8]([C:35]2[S:36][CH:37]=[C:38]([C:40]([F:42])([F:41])[F:43])[N:39]=2)[CH:7]=1)[CH3:2]

Participants

4

Reactant 3

HCID 702EthanolHCID 6329MethylamineHCID 59415791(S)-ethyl 6-(6-(3-ethylureido)-4-(4-(trifluoromethyl)thiazol-2-yl)pyridin-3-yl)-1-(1-hydroxy-4-methylpentan-2-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylate

Product 1

HCID 59415954(S)-6-(6-(3-ethylureido)-4-(4-(trifluoromethyl)thiazol-2-yl)pyridin-3-yl)-1-(1-hydroxy-4-methylpentan-2-yl)-N-methyl-4-oxo-1,4-dihydroquinoline-3-carboxamideYield 80%

Procedure

A solution of (S)-ethyl 6-(6-(3-ethylureido)-4-(4-(trifluoromethyl)thiazol-2-yl)pyridin-3-yl)-1-(1-hydroxy-4-methylpentan-2-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylate (Example 119, 280 mg, 0.44 mmol) in 33 wt. % methylamine solution in absolute ethanol (4 mL, 32.13 mmol) was heated in the microwave at 80° C. for 30 min The reaction mixture was concentrated under reduced pressure. Purification via column chromatography to provide (silica, 95:5 methylene chloride/methanol) gave (S)-6-(6-(3-ethylureido)-4-(4-(trifluoromethyl)thiazol-2-yl)pyridin-3-yl)-1-(1-hydroxy-4-methylpentan-2-yl)-N-methyl-4-oxo-1,4-dihydroquinoline-3-carboxamide as a light yellow solid (219.2 mg, 80%).

Workup

  1. concentrationwas concentrated under reduced pressure
  2. customPurification via column chromatography
  3. customto provide (silica, 95:5 methylene chloride/methanol)

Sources & evidence

ORD record
ord-c0accc70df304c7b8f0d6791e8735684
Source dataset
uspto-grants-2012_10
Patent number
US08283361B2

Reaction notes

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