HCID 874532, 화합물 → HCID 69748795, 화합물

HRID 1062376노트

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HRID 1062376 반응식
[Cl:1][C:2]1[CH:7]=[C:6]([SH:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10](=[O:18])[C@:11]([OH:17])([CH3:16])[C:12]([F:15])([F:14])[F:13].I[C:20]1[CH:25]=[CH:24][C:23]([S:26]([N:29]2[CH2:33][CH2:32][CH2:31][CH2:30]2)(=[O:28])=[O:27])=[CH:22][CH:21]=1.C[O-].[Na+]>CC(N(C)C)=O.[Cu]Cl>[Cl:1][C:2]1[CH:7]=[C:6]([S:8][C:20]2[CH:25]=[CH:24][C:23]([S:26]([N:29]3[CH2:30][CH2:31][CH2:32][CH2:33]3)(=[O:28])=[O:27])=[CH:22][CH:21]=2)[CH:5]=[CH:4][C:3]=1[NH:9][C:10](=[O:18])[C@:11]([OH:17])([CH3:16])[C:12]([F:15])([F:13])[F:14]

참가 물질

6

반응물 3

HCID 874532HCID 874532, 화합물HCID 10942334Sodium MethoxideHCID 54333950HCID 54333950, 화합물

생성물 1

HCID 69748795HCID 69748795, 화합물수율 44.9%

시약·촉매·용매 2

HCID 62652Cuprous chloride촉매HCID 31374Dimethylacetamide용매

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온도
150 °C

실험 절차

Copper (1) chloride (0.038 g) was added to a mixture of (R)-N-(2-chloro-4-mercaptophenyl)-2-hydroxy-2-methyl-3,3,3-trifluoropropanamide (Example 210) (0.21 g), N-(4-iodobenzenesulphonyl)pyrrolidine (0.258 g) and sodium methoxide (0.042 g) in DMA (5 ml). The mixture was heated at 150° C. with stirring for 4 hours then cooled and the DMA removed by evaporation. Ethyl acetate (20 ml) and water (20 ml) was added and the mixture was filtered. The aqueous layer was extracted with ethyl acetate (3×20 ml) and the organic layers were combined and dried. Volatile material was removed by evaporation and the residue was purified on a silica gel Mega Bond Elut column, eluting with methanol/DCM 0-10% to give the title compound (0.16 g) as a solid. NMR (CDCl3): 1.75 (s, 3H), 1.75-1.85 (m, 4H), 3.2-3.3 (m, 4H), 4.0 (s, 1H), 7.2-7.3 (m, 2H), 7.4-7.45 (m, 1H), 7.6 (s, 1), 7.7 (d, 2H), 8.45 (d, 1H), 9.15 (s, 1H); MS (ESP−): 507.

후처리

  1. temperaturethen cooled
  2. customthe DMA removed by evaporation
  3. additionEthyl acetate (20 ml) and water (20 ml) was added
  4. filtrationthe mixture was filtered
  5. extractionThe aqueous layer was extracted with ethyl acetate (3×20 ml)
  6. customdried
  7. customVolatile material was removed by evaporation
  8. customthe residue was purified on a silica gel Mega Bond Elut column
  9. washeluting with methanol/DCM 0-10%

출처 및 근거

ORD 기록
ord-acd0253acaae4a3d8aaba5c09bd405f7
출처 데이터셋
uspto-grants-2005_11
특허 번호
US06960688B2

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