Tert-Butylamine → 5-{[(1,1-Dimethylethyl)amino]sulfonyl}-2,4-difluorobenzoic acid

HRID 1992151Notes

Reaction equation

HRID 1992151 reaction equation
Cl[S:2]([C:5]1[C:6]([F:15])=[CH:7][C:8]([F:14])=[C:9]([CH:13]=1)[C:10]([OH:12])=[O:11])(=[O:4])=[O:3].[C:16]([NH2:20])([CH3:19])([CH3:18])[CH3:17].CCN(C(C)C)C(C)C.ClC1C(S(NC)(=O)=O)=CC=C(Cl)C=1C(O)=O>>[CH3:17][C:16]([NH:20][S:2]([C:5]1[C:6]([F:15])=[CH:7][C:8]([F:14])=[C:9]([CH:13]=1)[C:10]([OH:12])=[O:11])(=[O:4])=[O:3])([CH3:19])[CH3:18]

Participants

5

Reactant 4

HCID 6385Tert-ButylamineHCID 81531DiisopropylethylamineHCID 107535965-(Chlorosulfonyl)-2,4-difluorobenzoic acidHCID 290399082,6-Dichloro-3-(methylsulfamoyl)benzoic acid

Product 1

HCID 167764165-{[(1,1-Dimethylethyl)amino]sulfonyl}-2,4-difluorobenzoic acid

Procedure

Prepared from a mixture of 5-(chlorosulfonyl)-2,4-difluorobenzoic acid (200 mg, 0.78 mmol, 1 equiv), tert-butyl amine (98 mL, 0.94 mmol, 1.2 equiv) and DIEA (280 μL, 1.56 mmol, 2 equiv) following the general procedure for 2,6-dichloro-3-[(methylamino)sulfonyl]benzoic acid 880-1b. The crude reaction mixture was carried on without further purification.

Workup

  1. customThe crude reaction mixture
  2. customwas carried on without further purification

Sources & evidence

ORD record
ord-7f50573748d14f9ea20e5023719e931f
Source dataset
uspto-grants-2010_01
Patent number
US07645771B2

Reaction notes

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