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Water → 4-[4-(3,5-dichloro-phenyl)-4-trifluoromethyl-4,5-dihydro-3H-pyrrol-2-yl]-2-methyl-N-thietan-3-yl-benzamide

HRID 1844646
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HRID 1844646 반응식
CS[C:3](=[N:18][CH2:19][Si](C)(C)C)[C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:16])[NH:11][CH:12]2[CH2:15][S:14][CH2:13]2)=[C:6]([CH3:17])[CH:5]=1.[Cl:24][C:25]1[CH:30]=[C:29]([C:31]([C:33]([F:36])([F:35])[F:34])=[CH2:32])[CH:28]=[C:27]([Cl:37])[CH:26]=1.O.O.O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O>C1COCC1>[Cl:24][C:25]1[CH:30]=[C:29]([C:31]2([C:33]([F:36])([F:34])[F:35])[CH2:19][N:18]=[C:3]([C:4]3[CH:9]=[CH:8][C:7]([C:10]([NH:11][CH:12]4[CH2:15][S:14][CH2:13]4)=[O:16])=[C:6]([CH3:17])[CH:5]=3)[CH2:32]2)[CH:28]=[C:27]([Cl:37])[CH:26]=1
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참가 물질

6

반응물 4

HCID 962WaterHCID 11726816Tetrabutylammonium Fluoride TrihydrateHCID 231598231,3-Dichloro-5-(3,3,3-trifluoroprop-1-en-2-yl)benzeneHCID 675060713-methyl-4-(thietan-3-ylcarbamoyl)-N-trimethylsilanylmethyl-thiobenzimidic acid methyl ester

생성물 1

HCID 666553094-[4-(3,5-dichloro-phenyl)-4-trifluoromethyl-4,5-dihydro-3H-pyrrol-2-yl]-2-methyl-N-thietan-3-yl-benzamide
수율 94%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a solution of 3-methyl-4-(thietan-3-ylcarbamoyl)-N-trimethylsilanylmethyl-thiobenzimidic acid methyl ester (Example I19) (16 mg) and 1,3-dichloro-5-(1-trifluoromethyl-vinyl)-benzene (see WO 2007/125984) (12 mg) in THF (2 ml) was added at −5° C. tetrabutylammonium fluoride trihydrate (TBAF) (0.41 g) dissolved in THF (1.5 ml). The reaction mixture was stirred at ambient temperature for 16 hours. Water was added and the mixture was extracted twice with ethyl acetate. The combined organic phases were washed with brine, dried over sodium sulfate and concentrated. The residue was purified by chromatography on silica gel (eluent: ethyl acetate/heptanes 1:2) to give 4-[4-(3,5-dichloro-phenyl)-4-trifluoromethyl-4,5-dihydro-3H-pyrrol-2-yl]-2-methyl-N-thietan-3-yl-benzamide (20 mg). 1H-NMR (400 MHz, CDCl3): 7.75-7.25 (m, 6H), 6.30 (s, 1H), 5.45 (m, 1H), 4.90 (d, 1H), 4.45 (d, 1H), 3.82 (d, 1H), 3.55-3.38 (m, 5H), 2.48 (s, 3H) ppm.

후처리

  1. customwas added at −5° C.
  2. extractionthe mixture was extracted twice with ethyl acetate
  3. washThe combined organic phases were washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography on silica gel (eluent: ethyl acetate/heptanes 1:2)

출처 및 근거

ORD 기록
ord-2bdaab1973c043679012a13b8dca2c26
출처 데이터셋
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08946447B2

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