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

HRID 429769Notes

Reaction equation

HRID 429769 reaction equation
[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

Participants

5

Reactant 2

HCID 10686541(2R,3R)-3-(2,4-Difluorophenyl)-3-hydroxy-2-methyl-4-(1H-1,2,4-triazol-1-yl)thiobutyramideHCID 18353418Ethanone, 2-bromo-1-[4-(1,2,3-thiadiazol-4-yl)phenyl]-

Product 1

HCID 10206981HCID 10206981, compoundYield 45%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-28521b6502a14206bb43ed5eb90842d2
Source dataset
uspto-grants-2001_11
Patent number
US06319933B1

Reaction notes

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