1,4-Dideoxy-1,4-iminothreitol → 4-((3S,4S)-3,4-Dihydroxypyrrolidin-1-yl)-3-(thiazol-5-yl)-N-(4-(trifluoromethoxy)phenyl)benzamide

HRID 525644

反応式

HRID 525644 の反応式
F[C:2]1[CH:21]=[CH:20][C:5]([C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][C:16]([F:19])([F:18])[F:17])=[CH:11][CH:10]=2)=[O:7])=[CH:4][C:3]=1[C:22]1[S:26][CH:25]=[N:24][CH:23]=1.[NH:27]1[CH2:31][C@H:30]([OH:32])[C@@H:29]([OH:33])[CH2:28]1>CS(C)=O>[OH:33][C@@H:29]1[C@@H:30]([OH:32])[CH2:31][N:27]([C:2]2[CH:21]=[CH:20][C:5]([C:6]([NH:8][C:9]3[CH:14]=[CH:13][C:12]([O:15][C:16]([F:19])([F:18])[F:17])=[CH:11][CH:10]=3)=[O:7])=[CH:4][C:3]=2[C:22]2[S:26][CH:25]=[N:24][CH:23]=2)[CH2:28]1

参加物

4

反応物 2

HCID 1461981,4-Dideoxy-1,4-iminothreitolHCID 899067714-fluoro-3-(thiazol-5-yl)-N-(4-(trifluoromethoxy)phenyl)benzamide

生成物 1

HCID 1180448044-((3S,4S)-3,4-Dihydroxypyrrolidin-1-yl)-3-(thiazol-5-yl)-N-(4-(trifluoromethoxy)phenyl)benzamide

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

A solution of 4-fluoro-3-(thiazol-5-yl)-N-(4-(trifluoromethoxy)phenyl)benzamide (Stage 1.1, 60 mg, 0.13 mmol), (3S,4S)-pyrrolidine-3,4-diol (28.2 mg. 0.273 mmol) and TEA (76 μL, 0.546 mmol) in DMSO (103 μL) was stirred at 105° C. for 90 h. The solvent was evaporated off under reduced pressure and the crude product was purified by preparative SFC (Column Diol, from 22% to 27% in 10 min) to afford the title compound as a yellow powder. UPLC-MS (Condition 1) tR=2.18 min, m/z=466.0 [M+H]+, m/z=464.1 [M−H]−; 1H-NMR (400 MHz, DMSO-d6) δ ppm 2.86 (d, J=10.51 Hz, 2H) 3.36 (dd, J=10.51, 3.67 Hz, 2H) 3.90 (br. s, 2H) 5.05 (br. s, 2H) 6.93 (d, J=8.80 Hz, 1H) 7.33 (d, J=8.56 Hz, 2H) 7.78-7.98 (m, 5H) 9.16 (s, 1H) 10.12 (s, 1H).

後処理

  1. customThe solvent was evaporated off under reduced pressure
  2. customthe crude product was purified by preparative SFC (Column Diol, from 22% to 27% in 10 min)

出典と根拠

ORDレコード
ord-609ce7b5f8f944cda9374dcc4844fd94
出典データセット
uspto-grants-2016_05
特許番号
US09340537B2

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