Potassium Hydroxide → 6-(Methylsulfonyl)-3-{[4-(1-pyrrolidinyl)-1-piperidinyl]methyl}-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylic acid

HRID 245237Notes

Reaction equation

HRID 245237 reaction equation
[OH-].[K+].[CH3:3][S:4]([C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[N:13]=[C:12]([C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[CH:18]=1)[C:11]([CH2:27][N:28]1[CH2:33][CH2:32][CH:31]([N:34]3[CH2:38][CH2:37][CH2:36][CH2:35]3)[CH2:30][CH2:29]1)=[C:10]2[C:39]([O:41]C)=[O:40])(=[O:6])=[O:5]>CO.O>[CH3:3][S:4]([C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[N:13]=[C:12]([C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:24])[F:25])[CH:18]=1)[C:11]([CH2:27][N:28]1[CH2:29][CH2:30][CH:31]([N:34]3[CH2:35][CH2:36][CH2:37][CH2:38]3)[CH2:32][CH2:33]1)=[C:10]2[C:39]([OH:41])=[O:40])(=[O:6])=[O:5]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 67419178Methyl 6-(methylsulfonyl)-3-{[4-(1-pyrrolidinyl)-1-piperidinyl]methyl}-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate

Product 1

HCID 674194336-(Methylsulfonyl)-3-{[4-(1-pyrrolidinyl)-1-piperidinyl]methyl}-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylic acidYield 63.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Conditions

Temperature
65 °C

Procedure

Potassium hydroxide (0.551 g, 9.82 mmol) was added to an orange suspension of methyl 6-(methylsulfonyl)-3-{[4-(1-pyrrolidinyl)-1-piperidinyl]methyl}-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate (1.13 g, 1.963 mmol) in methanol (19.63 mL) and water (6.54 mL). The mixture was heated to 65° C. Additional methanol (10 mL) was added, and the mixture was heated overnight for 22 h. The mixture was cooled to room temperature, and the solvent was removed under reduced pressure. The mixture was acidified to pH 4-5 with 2N HCl. The solid was collected by filtration and dried to give 6-(methylsulfonyl)-3-{[4-(1-pyrrolidinyl)-1-piperidinyl]methyl}-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylic acid (0.700 g). The filtrate was concentrated to a volume of approximately 3 mL, and the solid precipitate was collected by filtration to afford additional 6-(methylsulfonyl)-3-{[4-(1-pyrrolidinyl)-1-piperidinyl]methyl}-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylic acid (0.153 g; 0.853 g total, 73% combined yield). MS (m/z) 562.2 (M+H+).

Workup

  1. temperaturethe mixture was heated overnight for 22 h
  2. temperatureThe mixture was cooled to room temperature
  3. customthe solvent was removed under reduced pressure
  4. filtrationThe solid was collected by filtration
  5. customdried

Sources & evidence

ORD record
ord-7a0c8c501de1451dbf41d23f706b29e5
Source dataset
uspto-grants-2014_02
Patent number
US08658636B2

Reaction notes

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