Trifluoroacetic acid → 6-[4-(Azetidin-3-yloxy)-3-methoxy-phenyl]-2-(4-chloro-phenyl)-6H-thieno[2,3-c]pyridin-7-one trifluoroacetate

HRID 2384916Notes

Reaction equation

C(OC([N:8]1[CH2:11][CH:10]([O:12][C:13]2[CH:18]=[CH:17][C:16]([N:19]3[CH:24]=[CH:23][C:22]4[CH:25]=[C:26]([C:28]5[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=5)[S:27][C:21]=4[C:20]3=[O:35])=[CH:15][C:14]=2[O:36][CH3:37])[CH2:9]1)=O)(C)(C)C.[F:38][C:39]([F:44])([F:43])[C:40]([OH:42])=[O:41]>>[F:38][C:39]([F:44])([F:43])[C:40]([OH:42])=[O:41].[NH:8]1[CH2:9][CH:10]([O:12][C:13]2[CH:18]=[CH:17][C:16]([N:19]3[CH:24]=[CH:23][C:22]4[CH:25]=[C:26]([C:28]5[CH:29]=[CH:30][C:31]([Cl:34])=[CH:32][CH:33]=5)[S:27][C:21]=4[C:20]3=[O:35])=[CH:15][C:14]=2[O:36][CH3:37])[CH2:11]1

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 689482573-{4-[2-(4-Chloro-phenyl)-7-oxo-7H-thieno[2,3-c]pyridin-6-yl]-2-methoxy-phenoxy}-azetidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 689537536-[4-(Azetidin-3-yloxy)-3-methoxy-phenyl]-2-(4-chloro-phenyl)-6H-thieno[2,3-c]pyridin-7-one trifluoroacetateYield 93%

Procedure

Dissolve 3-{4-[2-(4-chloro-phenyl)-7-oxo-7H-thieno[2,3-c]pyridin-6-yl]-2-methoxy-phenoxy}-azetidine-1-carboxylic acid tert-butyl ester (280 mg, 0.52 mmol) in trifluoroacetic acid (5 mL) and stir the solution at RT for 1 h. Concentrate the solution in vacuo and purify the crude material by flash chromatography, using 8% MeOH (2 N NH3) in CH2Cl2 as eluent, to give 213 mg (93%) of the title compound. LC-MS/ES m/z (35Cl) 439.0 [M+H]+.

Workup

concentrationConcentrate the solution in vacuo
custompurify the crude material by flash chromatography

Sources & evidence

ORD record: ord-a4024940dc41444680b2585b51fca938
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08263772B2

Reaction notes

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