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

HRID 2368426

反応式

HRID 2368426 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-1c576a8d17c5455bb136cf2ff0fd0853
出典データセット
uspto-grants-2014_04
特許番号
US08703761B2

関連ノート

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