Trifluoroacetic acid → 6-[4-(azetidin-3-yloxy)-3-methoxy-phenyl]-2-(4-chloro-phenyl)-5,6-dihydro-4H-thieno[2,3-c]pyridin-7-one

HRID 2384907Notes

Reaction equation

HRID 2384907 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[CH2:24][CH2:23][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.FC(F)(F)C(O)=O>ClCCl>[NH:8]1[CH2:9][CH:10]([O:12][C:13]2[CH:18]=[CH:17][C:16]([N:19]3[CH2:24][CH2:23][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

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 689491773-{4-[2-(4-Chloro-phenyl)-7-oxo-4,7-dihydro-5H-thieno[2,3-c]pyridin-6-yl]-2-methoxy-phenoxy}-azetidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 689510906-[4-(azetidin-3-yloxy)-3-methoxy-phenyl]-2-(4-chloro-phenyl)-5,6-dihydro-4H-thieno[2,3-c]pyridin-7-oneYield 78.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dissolve 3-{4-[2-(4-chloro-phenyl)-7-oxo-4,7-dihydro-5H-thieno[2,3-c]pyridin-6-yl]-2-methoxy-phenoxy}-azetidine-1-carboxylic acid tert-butyl ester (924 μmol, 500 mg) in dichloromethane (10 mL), add trifluoroacetic acid (5 mL), and stir the reaction at room temperature for 2 h. Concentrate the material in vacuo and partition the residue between 1N NaOH (10 mL) and CH2Cl2 (15 mL). Separate the organic portion and extract the aqueous portion with CH2Cl2 (3×10 mL). Dry the combined organics over Na2SO4, filter, and concentrate to dryness to afford 320 mg of 6-[4-(azetidin-3-yloxy)-3-methoxy-phenyl]-2-(4-chloro-phenyl)-5,6-dihydro-4H-thieno[2,3-c]pyridin-7-one as a white solid.

Workup

  1. customthe reaction at room temperature for 2 h
  2. concentrationConcentrate the material in vacuo
  3. custompartition the residue between 1N NaOH (10 mL) and CH2Cl2 (15 mL)
  4. customSeparate the organic portion
  5. extractionextract the aqueous portion with CH2Cl2 (3×10 mL)
  6. dry with materialDry the combined organics over Na2SO4
  7. filtrationfilter
  8. concentrationconcentrate to dryness

Sources & evidence

ORD record
ord-eda3feb8156647018d6be5d8e2f3b01c
Source dataset
uspto-grants-2012_09
Patent number
US08263772B2

Reaction notes

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