(2R,3R)-3-(2,4-Difluorophenyl)-3-hydroxy-2-methyl-4-(1H-1,2,4-triazol-1-yl)thiobutyramide → HCID 10206981, 화합물

HRID 429769노트

반응식

HRID 429769 반응식
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@@:9]([OH:21])([CH2:15][N:16]1[CH:20]=[N:19][CH:18]=[N:17]1)[C@@H:10]([CH3:14])[C:11]([NH2:13])=[S:12].Br[CH2:23][C:24]([C:26]1[CH:31]=[CH:30][C:29]([C:32]2[N:33]=[N:34][S:35][CH:36]=2)=[CH:28][CH:27]=1)=O>C(#N)C.C(OCC)(=O)C>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@:9]([OH:21])([C@H:10]([C:11]1[S:12][CH:23]=[C:24]([C:26]2[CH:27]=[CH:28][C:29]([C:32]3[N:33]=[N:34][S:35][CH:36]=3)=[CH:30][CH:31]=2)[N:13]=1)[CH3:14])[CH2:15][N:16]1[CH:20]=[N:19][CH:18]=[N:17]1

참가 물질

5

반응물 2

HCID 10686541(2R,3R)-3-(2,4-Difluorophenyl)-3-hydroxy-2-methyl-4-(1H-1,2,4-triazol-1-yl)thiobutyramideHCID 183534182-Bromo-1-[4-(1,2,3-thiadiazol-4-yl)phenyl]ethanone

생성물 1

HCID 10206981HCID 10206981, 화합물수율 45%

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 8857Ethyl Acetate용매

실험 절차

A mixture of (2R,3R)-3-(2,4-difluorophenyl)-3-hydroxy-2-methyl-4-(1H-1,2,4-triazol-1-yl)thiobutyramide (19.7 mg) and 2-bromo-1-[4-(1,2,3-thiadiazol-4-yl)phenyl]ethanone (27.4 mg) in acetonitrile (3.0 ml) was stirred at room temperature for 1.0 hour. The solution was diluted with ethyl acetate (10 ml), washed with saturated sodium hydrogen carbonate solution (5 ml) and brine (5 ml), dried over anhydrous sodium sulfate, then concentrated in vacuo. The mixture was purified by silica gel column chromatography developed by hexane-ethyl acetate (1:1) to give (2R,3R)-2-(2,4-difluorophenyl)-3-{4-[4-(1,2,3-thiadiazol-4-yl)phenyl]thiazol-2-yl}-1-(1H-1,2,4-triazol-1-yl)butan-2-ol as a pale yellow solid (14.1mg). EI-MS: m/z 497 (M+); 1H-NMR (CDCl3): δ 1.26(3H, d, J=6.9 Hz), 4.10(1H, q, J=6.9 Hz), 4.31(1H, d, J=14.3 Hz), 4.92(1H, d, J=14.3 Hz), 6.04(1H, s), 6.76˜6.87 (2H, m), 7.48˜7.58(1H, m), 7.58(1H, s), 7.68(1H, s), 7.92(1H, s), 8.06(2H, d, J=8.4Hz), 8.16(2H, d, J=8.4 Hz), 8.73(1H, s).

후처리

  1. washwashed with saturated sodium hydrogen carbonate solution (5 ml) and brine (5 ml)
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe mixture was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-28521b6502a14206bb43ed5eb90842d2
출처 데이터셋
uspto-grants-2001_11
특허 번호
US06319933B1

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