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

HRID 1778298노트

반응식

HRID 1778298 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 176Acetic Acid용매

반응 조건

온도
110 °C

실험 절차

(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.

후처리

  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

출처 및 근거

ORD 기록
ord-a25ca72027c24131a207b057a2d387fe
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09266835B2

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