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

HRID 1849825Notes

Reaction equation

HRID 1849825 reaction equation
C(C1(COC2C(C3CC3)=CC(C(O)=O)=C(F)C=2)C2CC3CC(CC1C3)C2)#N.[CH:28]1([C:31]2[C:32]([O:41][CH:42]3[CH2:47][CH2:46][C:45]([F:49])([F:48])[CH2:44][CH2:43]3)=[CH:33][C:34]([F:40])=[C:35]([CH:39]=2)[C:36](O)=[O:37])[CH2:30][CH2:29]1.CS(N)(=O)=O.[CH:55]1([S:58]([NH2:61])(=[O:60])=[O:59])[CH2:57][CH2:56]1>>[CH:28]1([C:31]2[C:32]([O:41][CH:42]3[CH2:47][CH2:46][C:45]([F:49])([F:48])[CH2:44][CH2:43]3)=[CH:33][C:34]([F:40])=[C:35]([CH:39]=2)[C:36]([NH:61][S:58]([CH:55]2[CH2:57][CH2:56]2)(=[O:60])=[O:59])=[O:37])[CH2:30][CH2:29]1

Participants

5

Reactant 4

HCID 72879MethanesulfonamideHCID 15765418CyclopropanesulfonamideHCID 867036554-((2-Cyanoadamantan-2-yl)methoxy)-5-cyclopropyl-2-fluorobenzoic acidHCID 867037125-Cyclopropyl-4-((4,4-difluorocyclohexyl)oxy)-2-fluorobenzoic acid

Product 1

HCID 867037135-cyclopropyl-N-(cyclopropylsulfonyl)-4-((4,4-difluorocyclohexyl)oxy)-2-fluorobenzamide

Procedure

Following the procedure as described in Example 332 Step 7 and making non-critical variations to replace 4-((2-cyanoadamantan-2-yl)methoxy)-5-cyclopropyl-2-fluorobenzoic acid with 5-cyclopropyl-4-((4,4-difluorocyclohexyl)oxy)-2-fluorobenzoic acid and to replace methanesulfonamide with cyclopropanesulfonamide, the title compound was obtained as a colorless solid (0.093 g, 48%): 1H NMR (300 MHz, DMSO-d6) δ 11.79 (br s, 1H), 7.13-7.06 (m, 2H), 4.78 (br s, 1H), 3.08-2.99 (m, 1H), 2.08-1.86 (m, 9H), 1.09-1.06 (m, 4H), 0.88-0.82 (m, 2H), 0.66-0.60 (m, 2H); 19F NMR (282 MHz, DMSO-d6) δ −92.1 (d, J=231 Hz, 1F), −98.5 (d, J=231 Hz, 1F), −112.5 (s, 1F); MS (ES−) m/z 416.10 (M−1).

Sources & evidence

ORD record
ord-3eed70feed9c4420a24bf94030523886
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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