(2-Amino-5-chloro-phenyl)-(6-methyl-pyridin-3-yl)methanone → N-[4-Chloro-2-(6-methyl-pyridine-3-carbonyl)-phenyl]-4-(1-methyl-1-oxazol-4-yl-ethyl)-benzenesulfonamide

HRID 29609Notes

Reaction equation

HRID 29609 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[C:9]([C:11]1[CH:12]=[N:13][C:14]([CH3:17])=[CH:15][CH:16]=1)=[O:10].[CH3:18][C:19]([C:26]1[CH:31]=[CH:30][C:29]([S:32](Cl)(=[O:34])=[O:33])=[CH:28][CH:27]=1)([C:21]1[N:22]=[CH:23][O:24][CH:25]=1)[CH3:20]>N1C=CC=CC=1>[Cl:8][C:5]1[CH:6]=[CH:7][C:2]([NH:1][S:32]([C:29]2[CH:28]=[CH:27][C:26]([C:19]([CH3:20])([C:21]3[N:22]=[CH:23][O:24][CH:25]=3)[CH3:18])=[CH:31][CH:30]=2)(=[O:33])=[O:34])=[C:3]([C:9]([C:11]2[CH:12]=[N:13][C:14]([CH3:17])=[CH:15][CH:16]=2)=[O:10])[CH:4]=1

Participants

4

Reactant 2

HCID 22327305(2-Amino-5-chloro-phenyl)-(6-methyl-pyridin-3-yl)methanoneHCID 597887344-(1-Methyl-1-oxazol-4-yl-ethyl)-benzenesulfonyl Chloride

Product 1

HCID 59788631N-[4-Chloro-2-(6-methyl-pyridine-3-carbonyl)-phenyl]-4-(1-methyl-1-oxazol-4-yl-ethyl)-benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Following the general procedure for synthesis of N-arylbenzenesulfonamides, 63 mg (0.26 mmol) of (2-Amino-5-chloro-phenyl)-(6-methyl-pyridin-3-yl)-methanone and 50 mg (0.1 7 mmol) of 4-(1-Methyl-1-oxazol-4-yl-ethyl)-benzenesulfonyl chloride were combined in 0.8 ml of anhydrous pyridine at 60° C. to give, after purification, the title product as a pale yellow solid: 1H NMR (CDCl3): δ (ppm): 1.54 (s, 6H), 2.63 (s, 3H), 7.22-7.30 (m, 2H), 7.32 (m, 2H), 7.55 (m, 1H), 7.61-7.63 (m, 2H), 7.70-7.80 (m, 3H), 8.49 (d, 1H), 9.95 (s, 1H); MS: (M+H)/z=496.0.

Workup

  1. customto give
  2. customafter purification

Sources & evidence

ORD record
ord-090bfd4f30814d3192c8eddf88d6c6c0
Source dataset
uspto-grants-2008_09
Patent number
US07420055B2

Reaction notes

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