Trifluoroacetic anhydride → HCID 67974979, compound

HRID 468869Notes

Reaction equation

HRID 468869 reaction equation
[CH:1]1([C:4]([NH:6][C:7]2[CH:16]=[C:15]3[C:10]([CH:11]=[C:12]([C:19]4[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:20]=4[CH3:26])[N+:13]([O-])=[C:14]3[CH3:17])=[CH:9][N:8]=2)=[O:5])[CH2:3][CH2:2]1.FC(F)(F)C(OC(=O)C(F)(F)F)=[O:30]>ClCCl>[F:25][C:23]1[CH:22]=[CH:21][C:20]([CH3:26])=[C:19]([C:12]2[CH:11]=[C:10]3[C:15]([CH:16]=[C:7]([NH:6][C:4]([CH:1]4[CH2:3][CH2:2]4)=[O:5])[N:8]=[CH:9]3)=[C:14]([CH2:17][OH:30])[N:13]=2)[CH:24]=1

Participants

4

Reactant 2

HCID 9845Trifluoroacetic anhydrideHCID 57411677HCID 57411677, compound

Product 1

HCID 67974979HCID 67974979, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a slurry of 7-(cyclopropanecarboxamido)-3-(5-fluoro-2-methylphenyl)-1-methyl-2,6-naphthyridine 2-oxide (100 mg, 0.3 mmol) in dichloromethane (3 mL) was added trifluoroacetic anhydride (0.08 mL, 0.57 mmol) and the reaction mixture was stirred at room temperature for 30 minutes. The mixture was diluted with dichloromethane (50 mL) and washed with saturated aqueous sodium bicarbonate solution (20 mL). The organic layer was separated, dried over sodium sulfate, filtered, and evaporated in vacuo to afford a residue that was purified by reverse phase HPLC (5-85% acetonitrile in water with 0.1% formic acid over 14 min) to afford the title compound as an off-white solid (50 mg, 50%). 1H NMR (400 MHz, DMSO) δ 11.13 (s, 1H), 9.31 (s, 1H), 8.89 (s, 1H), 8.06 (s, 1H), 7.43-7.33 (m, 2H), 7.19 (td, J=8.4, 2.6 Hz, 1H), 5.43 (t, J=5.4 Hz, 1H), 5.00 (d, J=5.4 Hz, 2H), 2.38 (s, 3H), 2.09 (m, 1H), 0.88 (m, 4H). LCMS (Method E): RT=4.553 min, M+H+=352.1.

Workup

  1. washwashed with saturated aqueous sodium bicarbonate solution (20 mL)
  2. customThe organic layer was separated
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customto afford a residue that
  7. customwas purified by reverse phase HPLC (5-85% acetonitrile in water with 0.1% formic acid over 14 min)

Sources & evidence

ORD record
ord-d657058a763b4aae84e79df9054bcfd0
Source dataset
uspto-grants-2014_01
Patent number
US08623889B2

Reaction notes

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