Trifluoroacetic acid → N-[4-cyano-3-(trifluoromethyl)phenyl]-2-[4-(4-ethoxy-6-oxo-1H-pyridin-3-yl)-2-fluorophenyl]acetamide

HRID 1050165Notes

Reaction equation

HRID 1050165 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:38])[CH2:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:19]=[N:20][C:21]([O:27]CC4C=CC(OC)=CC=4)=[CH:22][C:23]=3[O:24][CH2:25][CH3:26])=[CH:14][C:13]=2[F:37])=[CH:5][C:4]=1[C:39]([F:42])([F:41])[F:40])#[N:2].C(O)(C(F)(F)F)=O.[NH4+].[OH-]>C(Cl)Cl>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:38])[CH2:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]3[C:23]([O:24][CH2:25][CH3:26])=[CH:22][C:21](=[O:27])[NH:20][CH:19]=3)=[CH:14][C:13]=2[F:37])=[CH:5][C:4]=1[C:39]([F:41])([F:42])[F:40])#[N:2]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14923Ammonium HydroxideHCID 90423150N-(4-cyano-3-(trifluoromethyl)phenyl)-2-(4-(4-ethoxy-6-((4-methoxybenzyl)oxy)pyridin-3-yl)-2-fluorophenyl)acetamide

Product 1

HCID 78427301N-[4-cyano-3-(trifluoromethyl)phenyl]-2-[4-(4-ethoxy-6-oxo-1H-pyridin-3-yl)-2-fluorophenyl]acetamideYield 64.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-(4-cyano-3-(trifluoromethyl)phenyl)-2-(4-(4-ethoxy-6-((4-methoxybenzyl)oxy)pyridine-3-yl)-2-fluorophenyl)acetamide (870 mg, 1.501 mmol) in DCM (10 mL) was added TFA (1.157 mL, 15.01 mmol) at 0° C. The mixture was stirred at rt for 1 h. The mixture was basified with NH4OH (5 mL, 20%) to pH=8, filtered to give a solid, which was washed with H2O (5 mL) and dried to afford the product N-(4-cyano-3-(trifluoromethyl)phenyl)-2-(4-(4-ethoxy-6-oxo-1,6-dihydropyridin-3-yl)-2-fluorophenyl)acetamide (462.91 mg, 0.973 mmol, 64.8% yield): 1H NMR (400 MHz, CD3OD): δ 8.24 (s, 1H), 7.96-8.05 (m, 1H), 7.90-7.96 (m, 1H), 7.36-7.40 (m, 2H), 7.20-7.28 (m, 2H), 6.00 (s, 1H), 4.12 (q, J=7.2 Hz, 2H), 3.85 (s, 2H), 1.38 (t, J=7.2 Hz, 3H): LCMS (m/z): 459.9 (M+H).

Workup

  1. filtrationfiltered
  2. customto give a solid, which
  3. washwas washed with H2O (5 mL)
  4. customdried

Sources & evidence

ORD record
ord-ff496559e9b44c9294fd42c5fe123857
Source dataset
uspto-grants-2016_07
Patent number
US09382238B2

Reaction notes

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