Benzenesulfonyl chloride → HCID 58138403, compound

HRID 1469122Notes

Reaction equation

HRID 1469122 reaction equation
[F:1][C:2]1[C:3]([NH:9][C:10]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:11])=[N:4][C:5]([OH:8])=[N:6][CH:7]=1.[C:19]1([S:25](Cl)(=[O:27])=[O:26])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CC#N>[C:19]1([S:25]([N:6]2[CH:7]=[C:2]([F:1])[C:3]([NH:9][C:10]([NH:12][C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)=[O:11])=[N:4][C:5]2=[O:8])(=[O:27])=[O:26])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 7369Benzenesulfonyl chlorideHCID 178521964HCID 178521964, compound

Product 1

HCID 58138403HCID 58138403, compoundYield 32.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

To a suspension of 1-(5-fluoro-2-hydroxypyrimidin-4-yl)-3-phenylurea (0.200 g, 0.8 mmol) in anhydrous CH3CN (4 mL) was added BSA (0.487 g, 2.4 mmol), and the mixture was warmed to 70° C. and stirred for 1 h. The resulting solution was cooled to room temperature, treated with benzenesulfonyl chloride (0.156 g, 0.9 mmol), and the mixture was stirred for 12 h. The solvent was evaporated, and the residue was partitioned between EtOAc and brine. The organic phase was dried over MgSO4, filtered, and concentrated to give the crude product as a white solid. Recrystallization from EtOAc and heptane afforded 1-(1-benzenesulfonyl-5-fluoro-2-oxo-1,2-dihydropyrimidin-4-yl)-3-phenylurea as a white solid (0.100 g, 32%): mp 210-214° C.; 1H NMR (400 MHz, DMSO-d6) δ 11.26 (dd, J=3.7, 1.1 Hz, 1H), 10.87 (m, 1H), 8.65 (m, 1H), 8.10 (d, J=7.5 Hz, 2H), 7.85 (t, J=7.5 Hz, 1H), 7.71 (m, 2H), 7.45 (m, 2H), 7.34 (m, 2H), 7.10 (m, 1H); ESIMS m/z 389 ([M+H]+).

Workup

  1. additionwas added BSA (0.487 g, 2.4 mmol)
  2. temperatureThe resulting solution was cooled to room temperature
  3. stirringthe mixture was stirred for 12 h
  4. customThe solvent was evaporated
  5. customthe residue was partitioned between EtOAc and brine
  6. dry with materialThe organic phase was dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give the crude product as a white solid
  10. customRecrystallization from EtOAc and heptane

Sources & evidence

ORD record
ord-281d6b59318848d896ab6c29516cae36
Source dataset
uspto-grants-2015_04
Patent number
US09006259B2

Reaction notes

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