Trifluoroacetic acid → HCID 50902247, compound

HRID 2281851Notes

Reaction equation

HRID 2281851 reaction equation
FC(F)(F)C(O)=O.[F:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]([C:18]2[CH:23]=[N:22][C:21]([O:24][CH3:25])=[CH:20][N:19]=2)=[O:17])=[CH:11][C:10]=1[C@:26]12[CH2:34][O:33][C@H:32]([CH3:35])[C@H:31]1[C:30](=[O:36])[N:29]([CH3:37])[C:28]([NH:38]C(=O)OC(C)(C)C)=[N:27]2>C(Cl)Cl>[NH2:38][C:28]1[N:29]([CH3:37])[C:30](=[O:36])[C@@H:31]2[C@@H:32]([CH3:35])[O:33][CH2:34][C@:26]2([C:10]2[CH:11]=[C:12]([NH:15][C:16]([C:18]3[CH:23]=[N:22][C:21]([O:24][CH3:25])=[CH:20][N:19]=3)=[O:17])[CH:13]=[CH:14][C:9]=2[F:8])[N:27]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69937522HCID 69937522, compound

Product 1

HCID 50902247HCID 50902247, compoundYield 61.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (1 ml) was added to a stirred solution of tert-butyl ((4aS,5R,7aS)-7a-(2-fluoro-5-(5-methoxypyrazine-2-carboxamido)phenyl)-3,5-dimethyl-4-oxo-3,4,4a,5,7,7a-hexahydrofuro[3,4-d]pyrimidin-2-yl)carbamate (210 mg, 0.40 mmol) in DCM (2 mL) at RT. The mixture was stirred at RT for 1 h. The reaction mixture was evaporated and the residue was loaded on to a SCX cartridge (5 g). The cartridge was eluted with methanol (2×20 mL) and then 2M NH3 in MeOH (1×20 mL). The ammonia-methanol fraction was evaporated. The residue was treated with Et2O/hexanes and the resulting solid was collected by filtration and dried in vacuo to give the title compound (105 mg, colourless solid). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.31 (d, J=6.06 Hz, 3H) 2.99 (d, J=8.84 Hz, 1H) 3.10 (s, 3H) 4.02 (s, 3H) 4.05-4.14 (m, 1H) 4.14-4.22 (m, 2H) 6.04 (br. s., 2H) 7.16 (dd, J=10.99, 9.22 Hz, 1H) 7.70-7.83 (m, 2H) 8.41 (d, J=1.26 Hz, 1H) 8.88 (d, J=1.26 Hz, 1H) 10.58 (s, 1H).

Workup

  1. customThe reaction mixture was evaporated
  2. washThe cartridge was eluted with methanol (2×20 mL)
  3. customThe ammonia-methanol fraction was evaporated
  4. additionThe residue was treated with Et2O/hexanes
  5. filtrationthe resulting solid was collected by filtration
  6. customdried in vacuo

Sources & evidence

ORD record
ord-46ac3da78b8c42be90dcc61ec2de672e
Source dataset
uspto-grants-2015_09
Patent number
US09139594B2

Reaction notes

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