Methanesulfonyl chloride → HCID 19787881, compound

HRID 1656531Notes

Reaction equation

HRID 1656531 reaction equation
[NH2:1][C:2]1[C:7](=[O:8])[N:6]([CH2:9][C:10]([NH:12][CH:13]([CH:20]([CH3:22])[CH3:21])[C:14](=[O:19])[C:15]([F:18])([F:17])[F:16])=[O:11])[C:5]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[N:4][CH:3]=1.[CH3:29][S:30](Cl)(=[O:32])=[O:31]>O1CCCC1.C(N(CC)CC)C.C(OCC)(=O)C>[CH3:29][S:30]([NH:1][C:2]1[C:7](=[O:8])[N:6]([CH2:9][C:10]([NH:12][CH:13]([CH:20]([CH3:22])[CH3:21])[C:14](=[O:19])[C:15]([F:16])([F:18])[F:17])=[O:11])[C:5]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)=[N:4][CH:3]=1)(=[O:32])=[O:31]

Participants

6

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 19787906HCID 19787906, compound

Product 1

HCID 19787881HCID 19787881, compound

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-(5-amino-6-oxo-2-phenyl-1,6-dihydro-1-pyrimidinyl)-N-(3,3,3-trifluoro-1-isopropyl-2-oxopropyl)acetamide (0.345 g) in tetrahydrofuran (7 mL) and triethylamine (0.36 mL) at 0° C. was added methanesulfonoyl chloride (0.19 mL) and the resulting solution was allowed to stir overnight. The mixture was diluted with ethyl acetate and the solution washed (1N hydrochloric acid, water, 5% sodium bicarbonate). The organic layer was dried and evaporated. The residue was dissolved in tetrahydrofuran (1 mL), and to it was added 3N aqueous potassium hydroxide (0.07 mL). The solution was allowed to stir for 12 h. The reaction was quenched by addition of 1N hydrochloric acid and the product was extracted into ethyl acetate. The organic layer was washed (water, brine), and the solution was dried and evaporated. The resulting material was purified by chromatography, with tetrahydrofuran:dichloromethane (10:90) as the eluent, to provide 2-(5-methylsulfonylamino-6-oxo-2-phenyl-1,6-dihydro-1-pyrimidinyl)-N-(3,3,3-trifluoro-1-isopropyl-2-oxopropyl)acetamide as a white solid (0.146 g); NMR (DMSO/D2O): 9.35 (s,1), 8.84 (d,1), 8.01 (s,1), 7.50 (m,5), 4.68 (m,2), 4.55 (d,1), 3.10 (s,3), 2.16 (m,1), 0.89 (d,3), 0.83 (d,3).

Workup

  1. washthe solution washed (1N hydrochloric acid, water, 5% sodium bicarbonate)
  2. customThe organic layer was dried
  3. customevaporated
  4. dissolutionThe residue was dissolved in tetrahydrofuran (1 mL)
  5. additionto it was added 3N aqueous potassium hydroxide (0.07 mL)
  6. stirringto stir for 12 h
  7. customThe reaction was quenched by addition of 1N hydrochloric acid
  8. extractionthe product was extracted into ethyl acetate
  9. washThe organic layer was washed (water, brine)
  10. customthe solution was dried
  11. customevaporated
  12. customThe resulting material was purified by chromatography, with tetrahydrofuran:dichloromethane (10:90) as the eluent

Sources & evidence

ORD record
ord-214cb3c6633c4ac68003131e29f37948
Source dataset
uspto-grants-1993_10
Patent number
US05254558

Reaction notes

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