Methanesulfonamide → 4-(cyclohexylmethoxy)-5-cyclopropyl-2-fluoro-N-(N-methylsulfamoyl)benzamide

HRID 1849635Notes

Reaction equation

HRID 1849635 reaction equation
[CH:1]1([C:4]2[C:5]([O:14][CH2:15][C:16]3(C(F)(F)F)[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]3)=[CH:6][C:7]([F:13])=[C:8]([CH:12]=2)[C:9](O)=[O:10])[CH2:3][CH2:2]1.C1(COC2C(C3CC3)=CC(C(O)=O)=C(F)C=2)CCCCC1.CS(N)(=O)=O.[CH3:52][NH:53][S:54]([NH2:57])(=[O:56])=[O:55]>>[CH:16]1([CH2:15][O:14][C:5]2[C:4]([CH:1]3[CH2:3][CH2:2]3)=[CH:12][C:8]([C:9]([NH:57][S:54](=[O:56])(=[O:55])[NH:53][CH3:52])=[O:10])=[C:7]([F:13])[CH:6]=2)[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

5

Reactant 4

HCID 72879MethanesulfonamideHCID 13168287(Methylsulfamoyl)amineHCID 867034505-Cyclopropyl-2-fluoro-4-((1-(trifluoromethyl)-cyclohexyl)methoxy)benzoic acidHCID 867034874-(Cyclohexylmethoxy)-5-cyclopropyl-2-fluorobenzoic acid

Product 1

HCID 867034944-(cyclohexylmethoxy)-5-cyclopropyl-2-fluoro-N-(N-methylsulfamoyl)benzamide

Procedure

Following the procedure as described in Example 158 step 5, and making variations as required to replace 5-cyclopropyl-2-fluoro-4-((1-(trifluoromethyl)-cyclohexyl)methoxy)benzoic acid with 4-(cyclohexylmethoxy)-5-cyclopropyl-2-fluorobenzoic acid and to replace methanesulfonamide with (methylsulfamoyl)amine, the title compound was obtained (0.13 g, 25%) as a colorless solid: 1H NMR (300 MHz, CDCl3) δ8.76-8.65 (m, 1H), 7.57-7.50 (m, 1H), 6.62-6.52 (m, 1H), 5.31-5.22 (m, 1H), 3.86-3.78 (m, 2H), 2.79-2.74 (m, 3H), 2.11-1.99 (m, 1H), 1.95-1.65 (m, 6H), 1.41-1.03 (m, 5H), 0.98-0.89 (m, 2H), 0.69-0.61 (m, 2H); MS (ES−) m/z 383.3 (M−1).

Sources & evidence

ORD record
ord-b6fd9b658a8b4d518165ca97806bb0e6
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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