N-bromobutanimide → [2-Amino-4-(4-fluoro-phenyl)-thiazol-5-yl]-(4-fluoro-phenyl)-methanone

HRID 2368426

반응식

HRID 2368426 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH2:9][C:10]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)=[O:11])=[CH:4][CH:3]=1.C1C(=O)N(Br)C(=O)C1.[NH2:28][C:29]([NH2:31])=[S:30]>C(O)C>[NH2:31][C:29]1[S:30][C:9]([C:10]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)=[O:11])=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[N:28]=1

참가 물질

5

반응물 3

HCID 67184N-bromobutanimideHCID 738961,3-Propanedione, 1,3-bis(4-fluorophenyl)-HCID 2723790Thiourea

생성물 1

HCID 14435315[2-Amino-4-(4-fluoro-phenyl)-thiazol-5-yl]-(4-fluoro-phenyl)-methanone

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

1,3-Bis-(4-fluoro-phenyl)-propane-1,3-dione and NBS (1.05 eq) were heated neat at 60° C. for 10 minutes then cooled. The resulting mixture was dissolved in ethanol (0.2 M) and treated with thiourea (1.5 eq). It was heated at reflux for 15 hours and cooled to room temperature. It was evaporated to dryness and the residue was partioned between EtOAc and saturated NaHCO3. Organic fraction was dried over MgSO4, filtered and concentrated. The title compound was collected by trituration with heptanes. 1H NMR (400 MHz, DMSO-d6) 6.86-7.01 (m, 4H) 7.22-7.32 (m, 2H) 7.35-7.45 (m, 2H) 8.11 (br. s., 2H). LCMS Method A Rt=1.18 m/z 317.0 (M+1), 315 (M−1).

후처리

  1. temperaturethen cooled
  2. temperatureIt was heated
  3. temperatureat reflux for 15 hours
  4. customIt was evaporated to dryness
  5. dry with materialOrganic fraction was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe title compound was collected by trituration with heptanes

출처 및 근거

ORD 기록
ord-1c576a8d17c5455bb136cf2ff0fd0853
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08703761B2

연결된 노트

불러오는 중…