Lithium Hydroxide → 1-(2-(Dimethylamino)ethyl)-4-oxo-6-(6-(3-propylureido)-4-(4-(trifluoromethyl)thiazol-2-yl)pyridin-3-yl)-1,4-dihydroquinoline-3-carboxylic acid

HRID 2061821Notes

Reaction equation

HRID 2061821 reaction equation
[CH3:1][N:2]1[CH2:5][CH:4]([N:6]2[C:15]3[C:10](=[CH:11][C:12]([C:16]4[CH:17]=[N:18][C:19]([NH:31][C:32]([NH:34][CH2:35][CH2:36][CH3:37])=[O:33])=[CH:20][C:21]=4[C:22]4[S:23][CH:24]=[C:25]([C:27]([F:30])([F:29])[F:28])[N:26]=4)=[CH:13][CH:14]=3)[C:9](=[O:38])[C:8]([C:39]([O:41]CC)=[O:40])=[CH:7]2)[CH2:3]1.[OH-].[Li+]>O1CCCC1>[CH3:5][N:2]([CH3:1])[CH2:3][CH2:4][N:6]1[C:15]2[C:10](=[CH:11][C:12]([C:16]3[CH:17]=[N:18][C:19]([NH:31][C:32]([NH:34][CH2:35][CH2:36][CH3:37])=[O:33])=[CH:20][C:21]=3[C:22]3[S:23][CH:24]=[C:25]([C:27]([F:30])([F:28])[F:29])[N:26]=3)=[CH:13][CH:14]=2)[C:9](=[O:38])[C:8]([C:39]([OH:41])=[O:40])=[CH:7]1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 44540347Ethyl 1-(1-methylazetidin-3-yl)-4-oxo-6-(6-(3-propylureido)-4-(4-(trifluoromethyl)thiazol-2-yl)pyridin-3-yl)-1,4-dihydroquinoline-3-carboxylate

Product 1

HCID 594157331-(2-(Dimethylamino)ethyl)-4-oxo-6-(6-(3-propylureido)-4-(4-(trifluoromethyl)thiazol-2-yl)pyridin-3-yl)-1,4-dihydroquinoline-3-carboxylic acidYield 74.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 1-(2-(dimethylamino)ethyl)-4-oxo-6-(6-(3-propylureido)-4-(4-(trifluoromethyl)thiazol-2-yl)pyridin-3-yl)-1,4-dihydroquinoline-3-carboxylate (Example 150, 100 mg, 0.16 mmol) in tetrahydrofuran (2 mL) was added lithium hydroxide (1 M, 650 μL) and the mixture was stirred for 1 h at room temperature. The organics were removed under a stream of nitrogen and the precipitate that formed was isolated by filtration, washed with water (1 mL), and dried in a vacuum oven overnight at 40° C. to give 70 mg of yellowish solid.

Workup

  1. customThe organics were removed under a stream of nitrogen
  2. customthe precipitate that formed
  3. customwas isolated by filtration
  4. washwashed with water (1 mL)
  5. customdried in a vacuum oven overnight at 40° C.

Sources & evidence

ORD record
ord-bee6da60960249d5934bf01dd07fa8bb
Source dataset
uspto-grants-2012_10
Patent number
US08283361B2

Reaction notes

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