2,4-Dimethoxybenzenesulfonyl chloride → HCID 11655984, compound

HRID 252712Notes

Reaction equation

HRID 252712 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[S:11](Cl)(=[O:13])=[O:12].[NH2:15][C:16]1[CH:17]=[C:18]([C:23]2[S:27][C:26]([NH:28][C:29](=[O:31])[CH3:30])=[N:25][C:24]=2[CH3:32])[CH:19]=[N:20][C:21]=1[Cl:22]>N1C=CC=CC=1>[Cl:22][C:21]1[N:20]=[CH:19][C:18]([C:23]2[S:27][C:26]([NH:28][C:29](=[O:31])[CH3:30])=[N:25][C:24]=2[CH3:32])=[CH:17][C:16]=1[NH:15][S:11]([C:4]1[CH:5]=[CH:6][C:7]([O:9][CH3:10])=[CH:8][C:3]=1[O:2][CH3:1])(=[O:13])=[O:12]

Participants

4

Reactant 2

HCID 27346262,4-Dimethoxybenzenesulfonyl chlorideHCID 86244450N-[5-(5-amino-6-chloropyridin-3-yl)-4-methyl-1,3-thiazol-2-yl]acetamide

Product 1

HCID 11655984HCID 11655984, compoundYield 27.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2,4-Dimethoxyphenylsulfonyl chloride (J. Med. Chem., 1977, 20, 1235; 376 mg) was added to a stirred solution of N-[5-(5-amino-6-chloropyridin-3-yl)-4-methyl-1,3-thiazol-2-yl]acetamide (150 mg) in pyridine (1.5 mL) and the resultant solution was heated at 50° C. for 16 hours. The mixture was cooled to room temperature and concentrated by evaporation. The residue was purified by preparative HPLC on Kromasil C18 reversed-phase silica using a solvent gradient of 10% to 100% acetonitrile in water (containing 1% acetic acid) as eluent at a flow rate of about 10 mL/minute. The material so obtained was triturated under diethyl ether to give the title compound as a white solid (70 mg); 1H NMR Spectrum: (DMSOd6) 2.16 (s, 3H), 2.29 (s, 3H), 3.76 (s, 3H), 3.83 (s, 3H), 6.60 (m, 1H), 6.69 (d, 1H), 9.64 (d, 1H), 6.75 (d, 1H), 8.25 (br s, 1H), 9.80 (s, 1H); Mass Spectrum: M+H+ 483.

Workup

  1. concentrationconcentrated by evaporation
  2. customThe residue was purified by preparative HPLC on Kromasil C18 reversed-phase silica using a solvent gradient of 10% to 100% acetonitrile in water (containing 1% acetic acid) as eluent at a flow rate of about 10 mL/minute
  3. customThe material so obtained
  4. customwas triturated under diethyl ether

Sources & evidence

ORD record
ord-9877341aff524c58bf8b8332b80fd407
Source dataset
uspto-grants-2011_01
Patent number
US07868188B2

Reaction notes

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