Trifluoroacetic acid → HCID 54673534, compound

HRID 509550Notes

Reaction equation

HRID 509550 reaction equation
C(O)(C(F)(F)F)=O.[CH:8]([S:11]([C:14]1[CH:15]=[CH:16][C:17]([C:20]2[CH:21]=[C:22]([C:34]3[O:38][N:37]=[C:36]([C:39]4[CH:44]=[CH:43][C:42]([CH2:45][NH:46][CH3:47])=[CH:41][CH:40]=4)[CH:35]=3)[C:23]([NH:26]C(=O)OC(C)(C)C)=[N:24][CH:25]=2)=[N:18][CH:19]=1)(=[O:13])=[O:12])([CH3:10])[CH3:9]>C(Cl)Cl>[CH:8]([S:11]([C:14]1[CH:15]=[CH:16][C:17]([C:20]2[CH:21]=[C:22]([C:34]3[O:38][N:37]=[C:36]([C:39]4[CH:40]=[CH:41][C:42]([CH2:45][NH:46][CH3:47])=[CH:43][CH:44]=4)[CH:35]=3)[C:23]([NH2:26])=[N:24][CH:25]=2)=[N:18][CH:19]=1)(=[O:12])=[O:13])([CH3:10])[CH3:9]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68088960HCID 68088960, compound

Product 1

HCID 54673534HCID 54673534, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (1 mL, 12.98 mmol) was added to a stirred suspension of tert-butyl N-[5-(5-isopropylsulfonyl-2-pyridyl)-3-[3-[4-(methylaminomethyl)phenyl]isoxazol-5-yl]-2-pyridyl]carbamate (105 mg, 0.1863 mmol) in DCM (5 mL) and the reaction stirred at ambient temperature overnight. The solvent was removed in vacuo and the residue azeotroped with DCM (×2) and ether (×2). The reaction mixture was passed through a 2 g SCX-2 cartridge and washed with MeOH/DCM. The product was eluted by washing the cartridge with 2M NH3 in MeOH. The fractions were collected, concentrated in vacuo and the residue freeze-dried to give the title compound as a cream solid (30 mg, 35% Yield). NMR (400.0 DMSO) δ 1.22 (d, J=6.9 Hz, 6H), 2.30 (s, 3H), 3.56 (sept, 1H), 3.73 (s, 2H), 7.06 (br s, 2H), 7.51 (d, 2H), 7.63 (s, 1H), 7.93 (d, 2H), 8.24-8.31 (m, 2H), 8.74 (d, 1H), 8.99 (dd, 1H) and 9.02 (d, 1H) ppm; MS (ES+) 464.1.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue azeotroped with DCM (×2) and ether (×2)
  3. washwashed with MeOH/DCM
  4. washThe product was eluted
  5. washby washing the cartridge with 2M NH3 in MeOH
  6. customThe fractions were collected
  7. concentrationconcentrated in vacuo
  8. customthe residue freeze-dried

Sources & evidence

ORD record
ord-b559d8f85fcd421990a315e009b09b0b
Source dataset
uspto-grants-2015_08
Patent number
US09096584B2

Reaction notes

Loading…