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

HRID 1778298Notes

Reaction equation

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

Participants

Conditions

Temperature: 110 °C

Procedure

(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.

Workup

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

Sources & evidence

ORD record: ord-a25ca72027c24131a207b057a2d387fe
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09266835B2

Reaction notes

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