Trifluoroacetic acid → Trifluoroacetic acid

HRID 870982Notes

Reaction equation

HRID 870982 reaction equation
[F:1][C:2]1[C:7]2[O:8][CH2:9][C:10]3[C:15]([C:6]=2[CH:5]=[CH:4][C:3]=1[O:20]CC1C=CC(OC)=CC=1)=[CH:14][C:13]([NH:16][C:17](=[O:19])[CH3:18])=[N:12][CH:11]=3.[C:30]([OH:36])([C:32]([F:35])([F:34])[F:33])=[O:31]>ClCCl>[F:1][C:2]1[C:7]2[O:8][CH2:9][C:10]3[C:15]([C:6]=2[CH:5]=[CH:4][C:3]=1[OH:20])=[CH:14][C:13]([NH:16][C:17](=[O:19])[CH3:18])=[N:12][CH:11]=3.[C:30]([OH:36])([C:32]([F:35])([F:34])[F:33])=[O:31]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86695962HCID 86695962, compound

Product 2

HCID 6422Trifluoroacetic acidYield 45%HCID 136378616HCID 136378616, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of N-(7-fluoro-8-((4-methoxybenzyl)oxy)-5H-chromeno[3,4-c]pyridin-2-yl)acetamide (150 mg, 0.380 mmol) in dichloromethane (5 mL) was added TFA (0.059 mL, 0.761 mmol) at room temperature and the reaction mixture was stirred at rt for 2 h. After the completion of reaction the volatiles were removed under reduced pressure. The residue was washed with diethyl ether (7 mL) and stirred for 5 min. The solid was collected by vacuum filtration and dried under vacuum to yield N-(7-fluoro-8-hydroxy-5H-chromeno[3,4-c]pyridin-2-yl)acetamide, TFA (70 mg, 0.170 mmol, 45% yield) as a white solid. LCMS (ESI) m/e 275.0 [(M+H)+, calcd for C14H12FN2O3 275.1]; LC/MS retention time (Method E): tR=2.0 min.

Workup

  1. customAfter the completion of reaction the volatiles
  2. customwere removed under reduced pressure
  3. washThe residue was washed with diethyl ether (7 mL)
  4. stirringstirred for 5 min
  5. filtrationThe solid was collected by vacuum filtration
  6. customdried under vacuum

Sources & evidence

ORD record
ord-3ac6d46c88dd4fd3b9a862df5409e03e
Source dataset
uspto-grants-2015_03
Patent number
US08969564B2

Reaction notes

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