Propyl-2-thiourea → 4-(4-Fluorophenyl)-5-(4-methylsulfonylphenyl)-2-(1-propylamino) thiazole

HRID 1378590노트

반응식

HRID 1378590 반응식
Br[CH:2]([C:12]1[CH:17]=[CH:16][C:15]([S:18]([CH3:21])(=[O:20])=[O:19])=[CH:14][CH:13]=1)[C:3]([C:5]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][CH:6]=1)=O.[CH2:22]([NH:25][C:26]([NH2:28])=[S:27])[CH2:23][CH3:24]>C(O)C>[F:11][C:8]1[CH:9]=[CH:10][C:5]([C:3]2[N:28]=[C:26]([NH:25][CH2:22][CH2:23][CH3:24])[S:27][C:2]=2[C:12]2[CH:17]=[CH:16][C:15]([S:18]([CH3:21])(=[O:20])=[O:19])=[CH:14][CH:13]=2)=[CH:6][CH:7]=1

참가 물질

4

반응물 2

HCID 1615208Propyl-2-thioureaHCID 112340792-Bromo-1-(4-fluorophenyl)-2-(4-(methylsulfonyl)phenyl)ethanone

생성물 1

HCID 102220054-(4-Fluorophenyl)-5-(4-methylsulfonylphenyl)-2-(1-propylamino) thiazole수율 76%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

To a solution of 2-bromo-1-(4-fluorophenyl)-2-(4-methylsulfonylphenyl)ethanone (0.346 g, 0.932 mmol) (Example 26, Step 2) in ethanol (15 mL) in a 25 mL round bottom flask was added N-propylthiourea (0.116 g, 0.979 mmol) with stirring. The resulting solution was heated to reflux for 24 hours. The reaction was cooled to room temperature and concentrated in vacuo. The residue was dissolved in methylene chloride, washed successively with Na2CO3 (10% solution) and brine, dried over Na2SO4, filtered and reconcentrated in vacuo yielding 4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)-2-(1-propylamino) thiazole as a yellow crystalline solid (0.276 g, 76%): mp 181°-182° C. 1H NMR (DMSO-d6) 400 mHz 5 7.97 (t, J=5.37 Hz, 1H), 7.78 (d, J=8.79 Hz, H), 7.42 (dd, J=5.86, 8.79, 2H), 7.37 (d, J=8.79, H), 7.15 (t, J=8.79 Hz, 2H), 3.21 (q, J=6.84, H), 3.18 (s, 3H), 1.60 (m, 2H), 0.91 (t, J=7.33, H). MS (EI): m/z 390 (M+). HRMS Δ=2.4 mmu.

후처리

  1. temperatureThe resulting solution was heated
  2. temperatureto reflux for 24 hours
  3. concentrationconcentrated in vacuo
  4. dissolutionThe residue was dissolved in methylene chloride
  5. washwashed successively with Na2CO3 (10% solution) and brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered

출처 및 근거

ORD 기록
ord-ce25a412db7344eb9878091fd1dd5aa6
출처 데이터셋
uspto-grants-1997_09
특허 번호
US05668161

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