Sodium Hydroxide → 6-[(1-Methylethyl)sulfonyl]-3-[(3-methyl-4-oxo-1-piperidinyl)methyl]-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylic acid

HRID 245222

반응식

HRID 245222 반응식
[OH-].[Na+].[CH3:3][CH:4]([S:6]([C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[N:15]=[C:14]([C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[CH:20]=1)[C:13]([CH2:29][N:30]1[CH2:35][CH2:34][C:33](=[O:36])[CH:32]([CH3:37])[CH2:31]1)=[C:12]2[C:38]([O:40]C)=[O:39])(=[O:8])=[O:7])[CH3:5]>CO.O1CCCC1>[CH3:5][CH:4]([S:6]([C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[N:15]=[C:14]([C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[CH:20]=1)[C:13]([CH2:29][N:30]1[CH2:35][CH2:34][C:33](=[O:36])[CH:32]([CH3:37])[CH2:31]1)=[C:12]2[C:38]([OH:40])=[O:39])(=[O:7])=[O:8])[CH3:3]

참가 물질

5

반응물 2

HCID 14798Sodium HydroxideHCID 67416594Methyl 6-[(1-methylethyl)sulfonyl]-3-[(3-methyl-4-oxo-1-piperidinyl)methyl]-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate

생성물 1

HCID 674172316-[(1-Methylethyl)sulfonyl]-3-[(3-methyl-4-oxo-1-piperidinyl)methyl]-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylic acid수율 78.6%

시약·촉매·용매 2

HCID 887Methanol용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
50 °C

실험 절차

Sodium hydroxide (11.02 mL of a 2M solution, 22.04 mmol) was added to a yellow solution of methyl 6-[(1-methylethyl)sulfonyl]-3-[(3-methyl-4-oxo-1-piperidinyl)methyl]-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate (1.24 g, 2.204 mmol) in methanol (11.02 mL) and tetrahydrofuran (11.02 mL). The mixture was heated to 50° C. for 20 h. The mixture was cooled to room temperature, and the solvent was removed under reduced pressure. The residue was diluted with water (5 mL), and the solid precipitate was collected by filtration, washed with water (2×1 mL), and dried in a vacuum oven at 40° C. to afford 6-[(1-methylethyl)sulfonyl]-3-[(3-methyl-4-oxo-1-piperidinyl)methyl]-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylic acid (0.95 g, 72% yield). 1H NMR (400 MHz, DMSO-d6) δ8.53 (d, J=1.76 Hz, 1H), 8.10-8.18 (m, 2H), 7.96-8.05 (m, 2H), 7.83 (d, J=7.81 Hz, 1H), 7.72 (t, J=7.68 Hz, 1H), 3.71 (s, 2H), 3.49 (dt, J=6.77, 13.41 Hz, 1H), 2.68-2.78 (m, 2H), 2.08-2.32 (m, 3H), 1.92-2.03 (m, 2H), 1.22 (s, 3H), 1.20 (s, 3H), 0.70 (d, J=6.55 Hz, 3H); MS (m/z) 549.2 (M+H+).

후처리

  1. temperatureThe mixture was cooled to room temperature
  2. customthe solvent was removed under reduced pressure
  3. additionThe residue was diluted with water (5 mL)
  4. filtrationthe solid precipitate was collected by filtration
  5. washwashed with water (2×1 mL)
  6. customdried in a vacuum oven at 40° C.

출처 및 근거

ORD 기록
ord-e985ab1600e044dbb70109b4ac8d0f32
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08658636B2

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