Hydrochloric Acid → 4'-(4-(4-Propionylpiperazin-1-yl)-3(trifluoromethyl)phenylamino)-3,6'-biquinoline-3'-carboxylic acid

HRID 1944605Notes

Reaction equation

HRID 1944605 reaction equation
[C:1]([N:5]1[CH2:10][CH2:9][N:8]([C:11]2[CH:16]=[CH:15][C:14]([NH:17][C:18]3[C:27]4[C:22](=[CH:23][CH:24]=[C:25]([C:28]5[CH:29]=[N:30][C:31]6[C:36]([CH:37]=5)=[CH:35][CH:34]=[CH:33][CH:32]=6)[CH:26]=4)[N:21]=[CH:20][C:19]=3[C:38]([O:40]CC)=[O:39])=[CH:13][C:12]=2[C:43]([F:46])([F:45])[F:44])[CH2:7][CH2:6]1)(=[O:4])[CH2:2][CH3:3].[OH-].[Na+].Cl>C1COCC1.CO.O>[C:1]([N:5]1[CH2:6][CH2:7][N:8]([C:11]2[CH:16]=[CH:15][C:14]([NH:17][C:18]3[C:27]4[C:22](=[CH:23][CH:24]=[C:25]([C:28]5[CH:29]=[N:30][C:31]6[C:36]([CH:37]=5)=[CH:35][CH:34]=[CH:33][CH:32]=6)[CH:26]=4)[N:21]=[CH:20][C:19]=3[C:38]([OH:40])=[O:39])=[CH:13][C:12]=2[C:43]([F:44])([F:45])[F:46])[CH2:9][CH2:10]1)(=[O:4])[CH2:2][CH3:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 49782829Ethyl 4'-(4-(4-propionylpiperazin-1-yl)-3-(trifluoromethyl)phenylamino)-3,6'-biquinoline-3'-carboxylate

Product 1

HCID 497830314'-(4-(4-Propionylpiperazin-1-yl)-3(trifluoromethyl)phenylamino)-3,6'-biquinoline-3'-carboxylic acid

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

To a solution of compound 5.4 ethyl 4′-(4-(4-propionylpiperazin-1-yl)-3-(trifluoromethyl)phenylamino)-3,6′-biquinoline-3′-carboxylate in THF/MeOH/H2O (1:1:1, 6 mL) at room temperature was added NaOH (76 mg, 1.9 mmol, 5 equiv.). The resulting solution was stirred overnight. To the mixture was added HCl (1N) to adjust the pH to 4, and EtOAC (20 mL) to extract the product. The organic layer was concentrated to afford the desired product 5.5 4′-(4-(4-propionylpiperazin-1-yl)-3-(trifluoromethyl)phenylamino)-3,6′-biquinoline-3′-carboxylic acid. LC-MS (M+H): 622.21

Workup

  1. extractionto extract the product
  2. concentrationThe organic layer was concentrated

Sources & evidence

ORD record
ord-517efd0f328f497a92990b48e8bc1f44
Source dataset
uspto-grants-2013_03
Patent number
US08394818B2

Reaction notes

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