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

HRID 245237
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HRID 245237 반응식
[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]
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참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 887Methanol용매2회
HCID 962
Water
용매

반응 조건

온도
65 °C

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-7a0c8c501de1451dbf41d23f706b29e5
출처 데이터셋
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08658636B2

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