4-(4-Aminophenoxy)-N-methylpicolinamide → 4-[4-({[4-bromo-3-(pentafluoro-lambda6-sulfanyl)phenyl]carbamoyl}amino)phenoxy]-N-methylpyridine-2-carboxamide

HRID 1428415Notes

Reaction equation

HRID 1428415 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[C:9]=[O:10])=[CH:4][C:3]=1[S:11]([F:16])([F:15])([F:14])([F:13])[F:12].[NH2:17][C:18]1[CH:34]=[CH:33][C:21]([O:22][C:23]2[CH:28]=[CH:27][N:26]=[C:25]([C:29]([NH:31][CH3:32])=[O:30])[CH:24]=2)=[CH:20][CH:19]=1>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH:17][C:18]2[CH:34]=[CH:33][C:21]([O:22][C:23]3[CH:28]=[CH:27][N:26]=[C:25]([C:29]([NH:31][CH3:32])=[O:30])[CH:24]=3)=[CH:20][CH:19]=2)=[O:10])=[CH:4][C:3]=1[S:11]([F:16])([F:12])([F:13])([F:14])[F:15]

Participants

4

Reactant 2

HCID 166551294-(4-Aminophenoxy)-N-methylpicolinamideHCID 867012911-Bromo-4-isocyanato-2-(pentafluoro-lambda6-sulfanyl)benzene

Product 1

HCID 575208864-[4-({[4-bromo-3-(pentafluoro-lambda6-sulfanyl)phenyl]carbamoyl}amino)phenoxy]-N-methylpyridine-2-carboxamideYield 72%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The crude 1-bromo-4-isocyanato-2-(pentafluoro-λ6-sulfanyl)benzene obtained above was dissolved in DCM (70 mL). 4-(4-aminophenoxy)-N-methylpicolinamide (1.54 g, 6.34 mmol, 0.8 eq) was added at room temperature under N2. The mixture was stirred at room temperature for about 30 min, a lot of solid precipitated. DCM (30 mL) was added and made the mixture stirred at room temperature for 18 hrs. The solid was filtrated, washed with DCM (50 mL), dried under high vacuum to afford 2.6 g (yield 72%) of the title compound as a white solid.

Workup

  1. customa lot of solid precipitated
  2. additionDCM (30 mL) was added
  3. stirringstirred at room temperature for 18 hrs
  4. filtrationThe solid was filtrated
  5. washwashed with DCM (50 mL)
  6. customdried under high vacuum

Sources & evidence

ORD record
ord-e4e5ee69e62a499fa5569d359dd8d324
Source dataset
uspto-grants-2015_01
Patent number
US08937088B2

Reaction notes

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