2-Amino-5-[2,6-difluoro-4-(1-hydroxy-1-methylethyl)phenyl]thiophene-3-carboxamide → 5-[2,6-Difluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-({6-methyl-5-[(methylsulfonyl)amino]pyridin-2-yl}amino)thiophene-3-carboxamide

HRID 386028Notes

Reaction equation

HRID 386028 reaction equation
[NH2:1][C:2]1[S:3][C:4]([C:10]2[C:15]([F:16])=[CH:14][C:13]([C:17]([OH:20])([CH3:19])[CH3:18])=[CH:12][C:11]=2[F:21])=[CH:5][C:6]=1[C:7]([NH2:9])=[O:8].Cl[C:23]1[N:28]=[C:27]([CH3:29])[C:26]([N:30](S(C)(=O)=O)[S:31]([CH3:34])(=[O:33])=[O:32])=[CH:25][CH:24]=1>>[F:16][C:15]1[CH:14]=[C:13]([C:17]([OH:20])([CH3:18])[CH3:19])[CH:12]=[C:11]([F:21])[C:10]=1[C:4]1[S:3][C:2]([NH:1][C:23]2[CH:24]=[CH:25][C:26]([NH:30][S:31]([CH3:34])(=[O:32])=[O:33])=[C:27]([CH3:29])[N:28]=2)=[C:6]([C:7]([NH2:9])=[O:8])[CH:5]=1

Participants

3

Reactant 2

HCID 595256192-Amino-5-[2,6-difluoro-4-(1-hydroxy-1-methylethyl)phenyl]thiophene-3-carboxamideHCID 59526403N-(6-Chloro-2-methylpyridin-3-yl)-N-(methylsulfonyl)methanesulfonamide

Product 1

HCID 595257465-[2,6-Difluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-({6-methyl-5-[(methylsulfonyl)amino]pyridin-2-yl}amino)thiophene-3-carboxamide

Procedure

The title compounds were prepared in one pot as described in Example 1 using 2-amino-5-[2,6-difluoro-4-(1-hydroxy-1-methylethyl)phenyl]thiophene-3-carboxamide (150 mg, 0.48 mmol) and N-(6-chloro-2-methylpyridin-3-yl)-N(methylsulfonyl)methanesulfonamide (143 mg, 0.48 mmol) as starting materials. Mono and bis methylsulfonyl compounds were separated by column chromatography.

Workup

  1. customMono and bis methylsulfonyl compounds were separated by column chromatography

Sources & evidence

ORD record
ord-994c067532fc4635a67d2bcbe2a231b0
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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