Trifluoroacetic acid → HCID 50902333, compound

HRID 2281856Notes

Reaction equation

HRID 2281856 reaction equation
FC(F)(F)C(O)=O.[F:8][CH:9]([F:49])[C:10]1[N:11]=[CH:12][C:13]([C:16]([NH:18][C:19]2[CH:20]=[CH:21][C:22]([F:48])=[C:23]([C@:25]34[CH2:33][O:32][C@H:31]([C:34]([F:37])([F:36])[F:35])[C@H:30]3[C:29](=[O:38])[N:28]([CH3:39])[C:27]([NH:40]C(=O)OC(C)(C)C)=[N:26]4)[CH:24]=2)=[O:17])=[N:14][CH:15]=1>C(Cl)Cl>[NH2:40][C:27]1[N:28]([CH3:39])[C:29](=[O:38])[C@@H:30]2[C@@H:31]([C:34]([F:37])([F:36])[F:35])[O:32][CH2:33][C@:25]2([C:23]2[CH:24]=[C:19]([NH:18][C:16]([C:13]3[CH:12]=[N:11][C:10]([CH:9]([F:49])[F:8])=[CH:15][N:14]=3)=[O:17])[CH:20]=[CH:21][C:22]=2[F:48])[N:26]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86668925HCID 86668925, compound

Product 1

HCID 50902333HCID 50902333, compoundYield 95.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (1 mL) was added to a stirred solution of tert-butyl ((4aS,5S,7aS)-7a-(5-(5-(difluoromethyl)pyrazine-2-carboxamido)-2-fluorophenyl)-3-methyl-4-oxo-5-(trifluoromethyl)-3,4,4a,5,7,7a-hexahydrofuro[3,4-d]pyrimidin-2-yl)carbamate (92 mg, 0.15 mmol) in DCM (2 mL) at RT. After 1 h at this temperature the volatiles were removed in vacuo and the residue was azeotroped with PhMe (×2). The residue was then taken up in MeOH and loaded on to a SCX cartridge (5 g). The cartridge was eluted with MeOH (2×20 mL) and then 2M NH3 in MeOH (2×20 mL). The relevant fraction was evaporated to give the title compound (72 mg, beige solid). 1H NMR (400 MHz, MeOH-d4) δ ppm 3.25 (s, 3H) 3.80 (d, J=8.34 Hz, 1H) 4.29-4.34 (m, 1H) 4.35-4.40 (m, 1H) 4.62-4.71 (m, 1H) 6.95 (t, J=54.30 Hz, 1H) 7.18 (dd, J=11.62, 8.84 Hz, 1H) 7.80 (ddd, J=8.72, 4.17, 2.78 Hz, 1H) 7.89 (dd, J=6.82, 2.53 Hz, 1H) 9.02 (s, 1H) 9.40 (s, 1H).

Workup

  1. customAfter 1 h at this temperature the volatiles were removed in vacuo
  2. customthe residue was azeotroped with PhMe (×2)
  3. washThe cartridge was eluted with MeOH (2×20 mL)
  4. customThe relevant fraction was evaporated

Sources & evidence

ORD record
ord-398cb64672d34d85a635e5faafd1d5eb
Source dataset
uspto-grants-2015_09
Patent number
US09139594B2

Reaction notes

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