Methanesulfonamide → 5-chloro-N-(cyclopropylsulfonyl)-4-((4,4-difluorocyclohexyl)-oxy)-2-fluorobenzamide

HRID 1849806Notes

Reaction equation

HRID 1849806 reaction equation
CS(N)(=O)=O.[CH:6]1([S:9]([NH2:12])(=[O:11])=[O:10])[CH2:8][CH2:7]1.[Cl:13][C:14]1[C:15]([O:24][CH:25]2[CH2:30][CH2:29][C:28]([F:32])([F:31])[CH2:27][CH2:26]2)=[CH:16][C:17]([F:23])=[C:18]([CH:22]=1)[C:19](O)=[O:20]>CO>[Cl:13][C:14]1[C:15]([O:24][CH:25]2[CH2:26][CH2:27][C:28]([F:31])([F:32])[CH2:29][CH2:30]2)=[CH:16][C:17]([F:23])=[C:18]([CH:22]=1)[C:19]([NH:12][S:9]([CH:6]1[CH2:8][CH2:7]1)(=[O:11])=[O:10])=[O:20]

Participants

5

Reactant 3

HCID 72879MethanesulfonamideHCID 15765418Cyclopropanesulfonamide2×HCID 867036885-Chloro-4-((4,4-difluorocyclohexyl)oxy)-2-fluorobenzoic acid

Product 1

HCID 867036905-chloro-N-(cyclopropylsulfonyl)-4-((4,4-difluorocyclohexyl)-oxy)-2-fluorobenzamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Following the procedure as described in Example 332 Step 7 and making non-critical variations to replace methanesulfonamide with cyclopropanesulfonamide and to replace 4-(((1r,3r,5r,7r)-2-cyanoadamantan-2-yl)methoxy)-5-cyclopropyl-2-fluorobenzoic acid with 5-chloro-4-((4,4-difluorocyclohexyl)oxy)-2-fluorobenzoic acid and methanol with cyclopropyl sulfonamide, the title compound was obtained as a colorless solid (0.047 g, 31%): 1H NMR (300 MHz, DMSO-d6) δ 12.02 (br s, 1H), 7.75 (d, J=7.5 Hz, 1H), 7.37 (d, J=12.6 Hz, 1H), 4.85 (br s, 1H), 3.07-2.98 (m, 1H), 2.07-1.87 (m, 8H), 1.09-1.05 (m, 4H); 19F NMR (282 MHz, DMSO-d6) δ −92.3 (d, J=231 Hz, 1F), −98.5 (d, J=231 Hz, 1F), −109.9 (s, 1F); MS (ES−) m/z 410.0, 412.0 (M−1).

Sources & evidence

ORD record
ord-64f4d3d8cbe14b54b0ccc4f4d8883930
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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