Benzenesulfonyl chloride → HCID 57818855, compound

HRID 1500033Notes

Reaction equation

HRID 1500033 reaction equation
[F:1][C:2]1[C:3]([NH:9][C:10](=[O:12])[CH3:11])=[N:4][C:5]([OH:8])=[N:6][CH:7]=1.[C:13]1([S:19](Cl)(=[O:21])=[O:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>N1C=CC=CC=1>[C:10]([NH:9][C:3]1[C:2]([F:1])=[CH:7][N:6]=[C:5]([O:8][S:19]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)(=[O:21])=[O:20])[N:4]=1)(=[O:12])[CH3:11]

Participants

4

Reactant 2

HCID 7369Benzenesulfonyl chlorideHCID 178474475HCID 178474475, compound

Product 1

HCID 57818855HCID 57818855, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

N-(5-Fluoro-2-hydroxypyrimidin-4-yl)-acetamide* (200 mg, 1.17 mmol) was suspended in pyridine (5 mL) and stirred at ambient temperature. To the stirred suspension was added benzenesulfonyl chloride (226 mg, 1.29 mmol) and agitation was continued for 16 hours. The solvent was evaporated under a stream of nitrogen and the residue was suspended in dichloromethane (2-3 mL), placed directly onto a silica gel column, and eluted with ethyl acetate in petroleum ether (0-50% gradient) to isolate 180 mg, 0.58 mmol (49%) of the title compound as a white solid: mp 142-143° C.; 1H NMR (DMSO-d6) δ 10.96 (s, 1H), 8.67 (d, J=2.6 Hz, 1H), 8.12-8.06 (m, 2H), 7.86-7.79 (m, 1H), 7.73-7.65 (m, 2H), 2.98 (s, 3H); HPLC-MS (ESI) m/z 312 (M+H)+, 310 (M−H)−. *N-(5-Fluoro-2-hydroxypyrimidin-4-yl)-acetamide can be prepared through known literature methods. 1. Duschinsky, R., Fells, E., Hoffer, M. U.S. Pat. No. 3,309,359

Workup

  1. customThe solvent was evaporated under a stream of nitrogen
  2. washeluted with ethyl acetate in petroleum ether (0-50% gradient)

Sources & evidence

ORD record
ord-a708c1da789048ae9070477de2cd1a0f
Source dataset
uspto-grants-2015_12
Patent number
US09204653B2

Reaction notes

Loading…