Methanesulfonamide → N-(azetidin-1-ylsulfonyl)-5-cyclopropyl-4-(((1RS,6SR)-7,7-difluorobicyclo[4.1.0]heptan-1-yl)methoxy)-2-fluorobenzamide

HRID 1849848Notes

Reaction equation

HRID 1849848 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][CH2:42][C:43]34[C:49]([F:51])([F:50])[CH:48]3[CH2:47][CH2:46][CH2:45][CH2:44]4)=[CH:33][C:34]([F:40])=[C:35]([CH:39]=2)[C:36]([OH:38])=O)[CH2:30][CH2:29]1.CS(N)(=O)=O.[N:57]1([S:61]([NH2:64])(=[O:63])=[O:62])[CH2:60][CH2:59][CH2:58]1>>[N:57]1([S:61]([NH:64][C:36](=[O:38])[C:35]2[CH:39]=[C:31]([CH:28]3[CH2:29][CH2:30]3)[C:32]([O:41][CH2:42][C:43]34[C:49]([F:51])([F:50])[CH:48]3[CH2:47][CH2:46][CH2:45][CH2:44]4)=[CH:33][C:34]=2[F:40])(=[O:63])=[O:62])[CH2:60][CH2:59][CH2:58]1

Participants

5

Reactant 4

HCID 72879MethanesulfonamideHCID 450805661-AzetidinesulfonamideHCID 867036554-((2-Cyanoadamantan-2-yl)methoxy)-5-cyclopropyl-2-fluorobenzoic acidHCID 867036765-Cyclopropyl-4-((7,7-difluorobicyclo[4.1.0]heptan-1-yl)methoxy)-2-fluorobenzoic acid

Product 1

HCID 86703735N-(azetidin-1-ylsulfonyl)-5-cyclopropyl-4-(((1RS,6SR)-7,7-difluorobicyclo[4.1.0]heptan-1-yl)methoxy)-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-(((1SR,6RS)-7,7-difluorobicyclo-[4.1.0]heptan-1-yl)methoxy)-2-fluorobenzoic acid and to replace methanesulfonamide with azetidine-1-sulfonamide, the title compound was obtained as a white gum (0.051 g, 81%): 1H NMR (300 MHz, CDCl3) δ 8.65 (s, 1H), 7.64 (d, J=9.1 Hz, 1H), 6.54 (d, J=14.1 Hz, 1H), 4.25 (t, J=7.9 Hz, 4H), 3.98 (s, 2H), 2.32-2.22 (m, 2H), 2.09-2.00 (m, 1H), 1.96-1.57 (m, 4H), 1.49-1.25 (m, 5H), 0.98-0.92 (m, 2H), 0.72-0.67 (m, 2H); MS (ES+) m/z 459.1 (M+1).

Sources & evidence

ORD record
ord-6ddeb8462d1d40c19aeb5c97c2bfb652
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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