Potassium Hydroxide → HCID 67383517, compound

HRID 245261Notes

Reaction equation

[OH-].[K+].[CH2:3]([S:5]([C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][C:17]=1[O:18][CH3:19])[N:14]=[C:13]([C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=1)[C:12]([CH2:30][N:31]1[CH2:36][CH2:35][CH:34]([N:37]3[CH2:41][CH2:40][CH2:39][CH2:38]3)[CH2:33][CH2:32]1)=[C:11]2[C:42]([O:44]C)=[O:43])(=[O:7])=[O:6])[CH3:4]>CO.O>[CH2:3]([S:5]([C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][C:17]=1[O:18][CH3:19])[N:14]=[C:13]([C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:27])[F:28])[CH:21]=1)[C:12]([CH2:30][N:31]1[CH2:36][CH2:35][CH:34]([N:37]3[CH2:41][CH2:40][CH2:39][CH2:38]3)[CH2:33][CH2:32]1)=[C:11]2[C:42]([OH:44])=[O:43])(=[O:6])=[O:7])[CH3:4]

Participants

Conditions

Temperature: 65 °C

Procedure

Potassium hydroxide (0.364 g, 6.50 mmol) was added to a suspension of methyl 6-(ethylsulfonyl)-7-(methyloxy)-3-{[4-(1-pyrrolidinyl)-1-piperidinyl]methyl}-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate (0.805 g, 1.299 mmol) in methanol (12.99 mL) and water (4.33 mL). The mixture was heated to 65° C. for 3 d. The reaction mixture was cooled to room temperature, concentrated in vacuo, diluted with water (5 mL), and acidified to pH 4-5 with 2N HCl. The resulting precipitate was collected by filtration and dried to afford 6-(ethylsulfonyl)-7-(methyloxy)-3-{[4-(1-pyrrolidinyl)-1-piperidinyl]methyl}-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylic acid (0.487 g, 59% yield) as a tan solid. MS (m/z) 606.2 (M+H+).

Workup

temperatureThe reaction mixture was cooled to room temperature
concentrationconcentrated in vacuo
additiondiluted with water (5 mL)
filtrationThe resulting precipitate was collected by filtration
customdried

Sources & evidence

ORD record: ord-3187ba5fd0ae45cb9fbaf32a6920cc29
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08658636B2

Reaction notes

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