4-Chlorobenzenesulfonyl chloride → HCID 66973322, compound

HRID 1469115Notes

Reaction equation

HRID 1469115 reaction equation
[F:1][C:2]1[C:3]([N:9]=[CH:10][N:11]([CH3:13])[CH3:12])=[N:4][C:5]([OH:8])=[N:6][CH:7]=1.C(N(CC)CC)C.[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([S:28](Cl)(=[O:30])=[O:29])=[CH:24][CH:23]=1>ClCCl>[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([S:28]([N:6]2[CH:7]=[C:2]([F:1])[C:3]([N:9]=[CH:10][N:11]([CH3:13])[CH3:12])=[N:4][C:5]2=[O:8])(=[O:30])=[O:29])=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 73984-Chlorobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 178484257HCID 178484257, compound

Product 1

HCID 66973322HCID 66973322, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 25 mL screw-cap vial were added dichloromethane (CH2Cl2; 10 mL), N′-(5-fluoro-2-hydroxy-pyrimidin-4-yl)-N,N-dimethylformamidine (250 mg, 1.36 mmol), and triethylamine (Et3N, 300 mg, 3 mmol). To this mixture was added 4-chlorobenzenesulfonyl chloride (315 mg, 1.5 mmol), and the resulting mixture was shaken at room temperature for 3 h. The crude reaction mixture was partitioned between CH2Cl2 and brine, dried over MgSO4, filtered, and evaporated. The residue was purified by reverse phase chromatography to yield the title compound as a white solid (321 mg, 66%): mp 207-210° C.; 1H NMR (300 MHz, CDCl3) δ 8.75 (s, 1H), 8.08-8.02 (m, 3H), 7.53-7.47 (m, 2H), 3.23 (s, 3H), 3.21 (s, 3H); ESIMS m/z 360 ([M+H]+).

Workup

  1. customTo a 25 mL screw-cap vial
  2. customThe crude reaction mixture
  3. customwas partitioned between CH2Cl2 and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by reverse phase chromatography

Sources & evidence

ORD record
ord-5d9cad0f48914995896ddd5752d40443
Source dataset
uspto-grants-2015_04
Patent number
US09006259B2

Reaction notes

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