Trifluoromethanesulfonic acid → HCID 9978440, compound

HRID 1656527Notes

Reaction equation

HRID 1656527 reaction equation
C(OC([NH:11][C:12]1[C:17](=[O:18])[N:16]([CH2:19][C:20]([NH:22][CH:23]([CH:30]([CH3:32])[CH3:31])[C:24](=[O:29])[C:25]([F:28])([F:27])[F:26])=[O:21])[C:15]([C:33]2[S:34][CH:35]=[CH:36][CH:37]=2)=[N:14][CH:13]=1)=O)C1C=CC=CC=1.FC(F)(F)S(O)(=O)=O>ClCCl.C1(OC)C=CC=CC=1>[NH2:11][C:12]1[C:17](=[O:18])[N:16]([CH2:19][C:20]([NH:22][CH:23]([CH:30]([CH3:31])[CH3:32])[C:24](=[O:29])[C:25]([F:26])([F:27])[F:28])=[O:21])[C:15]([C:33]2[S:34][CH:35]=[CH:36][CH:37]=2)=[N:14][CH:13]=1

Participants

5

Reactant 2

HCID 62406Trifluoromethanesulfonic acidHCID 10414810HCID 10414810, compound

Product 1

HCID 9978440HCID 9978440, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 7519AnisoleSolvent

Procedure

To a solution of 2-[5-benzyloxycarbonylamino-6-oxo-2-(2-thienyl)-1,6-dihydro-1-pyrimidinyl]-N-(3,3,3-trifluoro-1-isopropyl-2-oxopropyl)acetamide in dichloromethane (35 mL) and anisole (1.2 mL) at 0° C. was added trifluoromethanesulfonic acid, and the resulting suspension was stirred for 15 minutes. The reaction was quenched by addition of sodium bicarbonate and the product extracted into ethyl acetate. The organic layer was washed (brine) and dried. The solvent was removed and the residue was purified by chromatography, with methanol:dichloromethane (gradient, 5:95, 7:93) as the eluent, to provide 2-[5-amino-6-oxo-2-(2-thienyl)-1,6-dihydro-1-pyrimidinyl]-N-(3,3,3-trifluoro-1-isopropyl-2-oxopropyl)acetamide as a yellow solid; 300 MHz NMR (DMSO/D2O): 7.94 (d,1), 7.65 (d,1), 7.30 (s,1), 7.22 (d,1), 7.02 (m,1), 4.84 (d,1), 4.69 (d,1), 4.07 (d,1), 2.24 (m,1), 0.89(d, 3), 0.76 (d,3).

Workup

  1. customThe reaction was quenched by addition of sodium bicarbonate
  2. extractionthe product extracted into ethyl acetate
  3. washThe organic layer was washed (brine)
  4. customdried
  5. customThe solvent was removed
  6. customthe residue was purified by chromatography, with methanol

Sources & evidence

ORD record
ord-229e523d1288483bb50eab2a604c6c8f
Source dataset
uspto-grants-1993_10
Patent number
US05254558

Reaction notes

Loading…