HCID 874532、化合物 → HCID 69748795、化合物

HRID 1062376ノート

反応式

HRID 1062376 の反応式
[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]

参加物

6

反応物 3

HCID 874532HCID 874532、化合物HCID 10942334Sodium MethoxideHCID 54333950HCID 54333950、化合物

生成物 1

HCID 69748795HCID 69748795、化合物収率 44.9%

試薬・触媒・溶媒 2

HCID 62652Cuprous chloride触媒HCID 31374Dimethylacetamide溶媒

反応条件

温度
150 °C

実験手順

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.

後処理

  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%

出典と根拠

ORDレコード
ord-acd0253acaae4a3d8aaba5c09bd405f7
出典データセット
uspto-grants-2005_11
特許番号
US06960688B2

反応ノート

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