Diisopropylethylamine → 4-[(5-chloro-6-isopropoxypyridin-3-yl)methoxy]-N-[(dimethylamino)sulfonyl]-2,5-difluorobenzamide

HRID 1525647Notes

Reaction equation

HRID 1525647 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:12][O:13][C:14]2[C:22]([F:23])=[CH:21][C:17]([C:18](O)=[O:19])=[C:16]([F:24])[CH:15]=2)[CH:5]=[N:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10].C(N(C(C)C)C(C)C)C.[CH3:34][N:35]([CH3:40])[S:36]([NH2:39])(=[O:38])=[O:37]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:12][O:13][C:14]2[C:22]([F:23])=[CH:21][C:17]([C:18]([NH:39][S:36]([N:35]([CH3:40])[CH3:34])(=[O:38])=[O:37])=[O:19])=[C:16]([F:24])[CH:15]=2)[CH:5]=[N:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 134472N,N-DimethylsulfamideHCID 666679654-((5-Chloro-6-isopropoxypyridin-3-yl)methoxy)-2,5-difluorobenzoic acid

Product 1

HCID 716160244-[(5-chloro-6-isopropoxypyridin-3-yl)methoxy]-N-[(dimethylamino)sulfonyl]-2,5-difluorobenzamide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To 4-((5-chloro-6-isopropoxypyridin-3-yl)methoxy)-2,5-difluorobenzoic acid (Preparation 9, 0.05 g, 0.14 mmol) in solution in DCM (5 mL) is added WSCDI (0.04 g, 0.21 mmol), DMAP (0.026 g, 0.21 mmol) and N-ethyl-N-isopropylpropan-2-amine (0.09 mL, 0.42 mmol). After 10 minutes was added N,N-dimethylsulfamide (0.026 g, 0.21 mmol) and the reaction was left at room temperature for 18 hours. The reaction mixture was concentrated in vacuo and purified using reverse phase preparative HPLC to afford the title compound.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. custompurified

Sources & evidence

ORD record
ord-09f472fcfdb645c0a525d5cb5d384146
Source dataset
uspto-grants-2015_07
Patent number
US09085517B2

Reaction notes

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