Benzenesulfonyl chloride → HCID 18470485, compound

HRID 2228923Notes

Reaction equation

HRID 2228923 reaction equation
[C:1]1([S:7](Cl)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][S:26][C:27]2[NH:32][C:31](=[O:33])[C:30]([CH2:34][C:35]3[CH:36]=[N:37][CH:38]=[CH:39][CH:40]=3)=[CH:29][N:28]=2)=[CH:14][CH:13]=1>N1C=CC=CC=1>[C:1]1([S:7]([N:28]2[CH:29]=[C:30]([CH2:34][C:35]3[CH:36]=[N:37][CH:38]=[CH:39][CH:40]=3)[C:31](=[O:33])[N:32]=[C:27]2[S:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][C:15]2[CH:16]=[CH:17][C:12]([Cl:11])=[CH:13][CH:14]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 7369Benzenesulfonyl chlorideHCID 18470406HCID 18470406, compound

Product 1

HCID 18470485HCID 18470485, compoundYield 18.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Benzenesulfonyl chloride (41 mg) was added to a solution of 2-(8-(4chlorophenyl)oct-1-yl)thio-5-(pyrid-3-ylmethyl)pyrimidin-4-one (103 mg) in pyridine (0.5 ml), and the mixture stirred overnight. Evaporation of the pyridine followed by chromatography (silica, 0-2% methanol in dichloromethane) gave 1-phenylsulfonyl-2-(8-(4-chlorophenyl)oct-1-yl)thio-5-(pyrid-3-ylmethyl)pyrimidin-4-one (25 mg). 1H-NMR (CDCl3) δ 1.2-1.5(8H, m), 1.5-1.8(4H, m), 2.56(2H, t), 2.92(2H, t), 3.87(2H, s), 7.08(2H, d), 7.15-7.8(7H, m), 7.95(2H, m), 8.29(1H, s) and 8.35-8.7(2H, bm).

Workup

  1. customEvaporation of the pyridine

Sources & evidence

ORD record
ord-c1d13d483db34ab09a9d71a656c6d7ad
Source dataset
uspto-grants-2002_07
Patent number
US06417192B1

Reaction notes

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