Trifluoroacetic acid → HCID 89815438, compound

HRID 715104Notes

Reaction equation

HRID 715104 reaction equation
C(O)(C(F)(F)F)=O.[C:8]([NH:11][C:12]1[CH:21]=[C:20]2[C:15]([CH:16]=[C:17]([C:23]3[C:24]([F:38])=[CH:25][C:26]([F:37])=[C:27]([NH:29]C(=O)OC(C)(C)C)[CH:28]=3)[C:18]([CH3:22])=[N:19]2)=[CH:14][N:13]=1)(=[O:10])[CH3:9]>C(Cl)Cl>[NH2:29][C:27]1[C:26]([F:37])=[CH:25][C:24]([F:38])=[C:23]([C:17]2[C:18]([CH3:22])=[N:19][C:20]3[C:15]([CH:16]=2)=[CH:14][N:13]=[C:12]([NH:11][C:8](=[O:10])[CH3:9])[CH:21]=3)[CH:28]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 89827691HCID 89827691, compound

Product 1

HCID 89815438HCID 89815438, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add TFA (5 mL, 64.9 mmol) to a solution of tert-butyl (5-(7-acetamido-2-methyl-1,6-naphthyridin-3-yl)-2,4-difluorophenyl)carbamate (0.63 g, 1.470 mmol) in DCM (5 mL), stir at RT for 16 h, then concentrate to dryness. Neutralize with satd. NaHCO3, extract with EtOAc/THF (1×), wash the organic layer with brine, dry over MgSO4 and concentrate to dryness. Triturate with THF/Hex, collect the solids via filtration and dry to afford the title compound (391 mg, 81%) as a tan solid. 1H NMR (400 MHz, DMSO-d6): δ 10.76 (s, 1H), 9.13 (d, J=0.84 Hz, 1H), 8.49 (s, 1H), 8.25 (s, 1H), 7.21 (dd, J=11.28, 9.65 Hz, 1H), 6.76 (dd, J=9.87, 7.72 Hz, 1H), 5.18 (s, 2H), 2.49 (s, 3H), 2.15 (s, 3H); MS (ESI) m/z: 329.1 (M+H+).

Workup

  1. concentrationconcentrate to dryness
  2. extractionNaHCO3, extract with EtOAc/THF (1×)
  3. washwash the organic layer with brine
  4. dry with materialdry over MgSO4
  5. concentrationconcentrate to dryness
  6. customTriturate with THF/Hex
  7. customcollect the solids
  8. filtrationvia filtration
  9. customdry

Sources & evidence

ORD record
ord-078b67b8e1014243a3663a8bdb3fe3a2
Source dataset
uspto-grants-2015_11
Patent number
US09187474B2

Reaction notes

Loading…