Methanesulfonamide → 5-cyclopropyl-4-((4,4-difluorocyclohexyl)methoxy)-2-fluoro-N-(N-methylsulfamoyl)benzamide

HRID 1849658Notes

Reaction equation

HRID 1849658 reaction equation
C1(C2C(OCC3(C(F)(F)F)CCCCC3)=CC(F)=C(C=2)C(O)=O)CC1.[CH:26]1([C:29]2[C:30]([O:39][CH2:40][CH:41]3[CH2:46][CH2:45][C:44]([F:48])([F:47])[CH2:43][CH2:42]3)=[CH:31][C:32]([F:38])=[C:33]([CH:37]=2)[C:34](O)=[O:35])[CH2:28][CH2:27]1.CS(N)(=O)=O.[CH3:54][NH:55][S:56]([NH2:59])(=[O:58])=[O:57]>>[CH:26]1([C:29]2[C:30]([O:39][CH2:40][CH:41]3[CH2:46][CH2:45][C:44]([F:48])([F:47])[CH2:43][CH2:42]3)=[CH:31][C:32]([F:38])=[C:33]([CH:37]=2)[C:34]([NH:59][S:56](=[O:58])(=[O:57])[NH:55][CH3:54])=[O:35])[CH2:28][CH2:27]1

Participants

5

Reactant 4

HCID 72879MethanesulfonamideHCID 13168287(Methylsulfamoyl)amineHCID 867034505-Cyclopropyl-2-fluoro-4-((1-(trifluoromethyl)-cyclohexyl)methoxy)benzoic acidHCID 867035175-Cyclopropyl-4-((4,4-difluorocyclohexyl)-methoxy)-2-fluorobenzoic acid

Product 1

HCID 867035225-cyclopropyl-4-((4,4-difluorocyclohexyl)methoxy)-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 5-cyclopropyl-4-((4,4-difluorocyclohexyl)-methoxy)-2-fluorobenzoic acid and to replace methanesulfonamide with (methylsulfamoyl)amine, the title compound was obtained (0.08 g, 29%) as a colorless solid: 1H NMR (300 MHz, CDCl3) δ8.77-8.64 (m, 1H), 7.62-7.51 (m, 1H), 6.65-6.52 (m, 1H), 5.30-5.18 (m, 1H), 3.95-3.85 (m, 2H), 2.83-2.72 (m, 3H), 2.28-1.66 (m, 8H), 1.57-1.42 (m, 2H), 1.01-0.90 (m, 2H), 0.71-0.60 (m, 2H); MS (ES+) m/z 421.1 (M+1).

Sources & evidence

ORD record
ord-a5e8d5b99e964faf924cef24f82e59a5
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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