Hydrochloric Acid → 6-((4-chlorophenyl)(thiazol-2-yl)methyl)-4-(4-(trifluoromethoxy)benzyl)quinolin-2(1H)-one

HRID 1778298ノート

反応式

HRID 1778298 の反応式
C([O:5][C:6]1[CH:15]=[C:14]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][C:24]([F:27])([F:26])[F:25])=[CH:19][CH:18]=2)[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:28]([C:35]3[CH:40]=[CH:39][C:38]([Cl:41])=[CH:37][CH:36]=3)([C:30]3[S:31][CH:32]=[CH:33][N:34]=3)O)[CH:12]=2)[N:7]=1)(C)(C)C.O.O.[Sn](Cl)Cl.Cl>CC(O)=O>[Cl:41][C:38]1[CH:39]=[CH:40][C:35]([CH:28]([C:30]2[S:31][CH:32]=[CH:33][N:34]=2)[C:11]2[CH:12]=[C:13]3[C:8](=[CH:9][CH:10]=2)[NH:7][C:6](=[O:5])[CH:15]=[C:14]3[CH2:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][C:24]([F:26])([F:27])[F:25])=[CH:19][CH:18]=2)=[CH:36][CH:37]=1

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 61436Stannous chloride dihydrateHCID 118323950(2-(Tert-butoxy)-4-(4-(trifluoromethoxy)benzyl)quinolin-6-yl)(4-chlorophenyl)(thiazol-2-yl)methanol

生成物 1

HCID 1183239686-((4-chlorophenyl)(thiazol-2-yl)methyl)-4-(4-(trifluoromethoxy)benzyl)quinolin-2(1H)-one

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

反応条件

温度
110 °C

実験手順

(2-(tert-Butoxy)-4-(4-(trifluoromethoxy)benzyl)quinolin-6-yl)(4-chlorophenyl)(thiazol-2-yl)methanol (55 mg, 0.0918 mmol) and tin(II) chloride dihydrate (83 mg, 0.367 mmol) were combined in AcOH (2 mL). HCl (conc. 36%, 0.115 mL) was then added. The solution was heated to 110° C. After 45 min the reaction was cooled to room temperature and concentrated. The residue was taken up in CH2Cl2 and washed with NaHCO3 (satd), dried (Na2SO4) and concentrated. The resulting residue was purified by silica column (70-80% EtOAc/hexanes) chromatography to yield 6-((4-chlorophenyl)(thiazol-2-yl)methyl)-4-(4-(trifluoromethoxy)benzyl)quinolin-2(1H)-one.

後処理

  1. temperatureAfter 45 min the reaction was cooled to room temperature
  2. concentrationconcentrated
  3. washwashed with NaHCO3 (satd)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customThe resulting residue was purified by silica column (70-80% EtOAc/hexanes) chromatography

出典と根拠

ORDレコード
ord-a25ca72027c24131a207b057a2d387fe
出典データセット
uspto-grants-2016_02
特許番号
US09266835B2

反応ノート

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