Pyridine → HCID 22291038, compound

HRID 1369495Notes

Reaction equation

HRID 1369495 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[NH2:6][C:7]1[CH:8]=[C:9]([CH:33]=[CH:34][CH:35]=1)[C:10]([NH:12][C:13]1[CH:14]=[CH:15][C:16]([CH3:32])=[C:17]([NH:19][C:20](=[O:31])[C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[C:23]([O:29][CH3:30])[CH:22]=2)[CH:18]=1)=[O:11].N1C=CC=CC=1>C(Cl)Cl>[CH3:1][S:2]([NH:6][C:7]1[CH:8]=[C:9]([CH:33]=[CH:34][CH:35]=1)[C:10]([NH:12][C:13]1[CH:14]=[CH:15][C:16]([CH3:32])=[C:17]([NH:19][C:20](=[O:31])[C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[C:23]([O:29][CH3:30])[CH:22]=2)[CH:18]=1)=[O:11])(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 22291106HCID 22291106, compound

Product 1

HCID 22291038HCID 22291038, compoundYield 84.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methanesulphonyl chloride (0.25 g) was added to a stirred mixture of N-[5-(3-aminobenzamido)-2-methylphenyl]-3,4-dimethoxybenzamide (0.84 g), pyridine (0.5 ml) and methylene chloride (25 ml) and the mixture was stirred at ambient temperature for 48 hours. The mixture was washed with 2N hydrochloric acid and with water, dried (MgSO4) and evaporated. The residue was triturated under diethyl ether and the resultant white solid was dried under vacuum at 60° C. There was thus obtained the title compound (0.85 g), m.p.>300° C.; NMR Spectrum: (DMSOd6) 2.18 (s, 3H), 3.03 (s, 3H), 3.82 (s, 6H), 7.06 (d, 1H), 7.23 (d, 1H), 7.4 (br d, 1H), 7.47 (t, 1H), 7.55 (br m, 2H), 7.63 (m, 1H), 7.66 (br d, 1H), 7.72 (d, 1H), 7.78 (d, 1H), 9.73 (br s, 1H), 9.91 (br s, 1H), 10.24 (br s, 1H); Mass Spectrum: M−H− 482.

Workup

  1. washThe mixture was washed with 2N hydrochloric acid and with water
  2. dry with materialdried (MgSO4)
  3. customevaporated
  4. customThe residue was triturated under diethyl ether
  5. customthe resultant white solid was dried under vacuum at 60° C

Sources & evidence

ORD record
ord-8a45241801fc4ed78f68de5118c79be0
Source dataset
uspto-grants-2003_06
Patent number
US06579872B1

Reaction notes

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