Methanesulfonamide → N-(azetidin-1-ylsulfonyl)-4-(bicyclo[4.1.0]heptan-3-ylmethoxy)-5-cyclopropyl-2-fluorobenzamide

HRID 1849816Notes

Reaction equation

HRID 1849816 reaction equation
C([C:3]1([CH2:13][O:14][C:15]2[C:23]([CH:24]3[CH2:26][CH2:25]3)=[CH:22][C:18]([C:19](O)=[O:20])=[C:17]([F:27])[CH:16]=2)[CH:10]2CC3[CH2:7][CH:8]([CH2:12][CH:4]1C3)[CH2:9]2)#N.C12CC1CCC(COC1C(C3CC3)=CC(C(O)=O)=C(F)C=1)C2.CS(N)(=O)=O.[N:55]1([S:59]([NH2:62])(=[O:61])=[O:60])[CH2:58][CH2:57][CH2:56]1>>[N:55]1([S:59]([NH:62][C:19](=[O:20])[C:18]2[CH:22]=[C:23]([CH:24]3[CH2:25][CH2:26]3)[C:15]([O:14][CH2:13][CH:3]3[CH2:10][CH2:9][CH:8]4[CH:12]([CH2:7]4)[CH2:4]3)=[CH:16][C:17]=2[F:27])(=[O:61])=[O:60])[CH2:58][CH2:57][CH2:56]1

Participants

5

Reactant 4

HCID 72879MethanesulfonamideHCID 450805661-AzetidinesulfonamideHCID 867036554-((2-Cyanoadamantan-2-yl)methoxy)-5-cyclopropyl-2-fluorobenzoic acidHCID 867036984-(Bicyclo[4.1.0]heptan-3-ylmethoxy)-5-cyclopropyl-2-fluorobenzoic acid

Product 1

HCID 86703700N-(azetidin-1-ylsulfonyl)-4-(bicyclo[4.1.0]heptan-3-ylmethoxy)-5-cyclopropyl-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 4-(bicyclo[4.1.0]heptan-3-ylmethoxy)-5-cyclopropyl-2- fluorobenzoic acid and making variations as required to replace methanesulfonamide with azetidine-1-sulfonamide, the title compound was obtained as solid (0.026 g, 5%): 1H NMR (300 MHz, CDCl3) δ 8.66 (d, J=16.5 Hz, 1H), 7.60 (d, J=9.1 Hz, 1H), 6.59 (d, J=14.5 Hz, 1H), 5.78-5.54 (m, 2H), 4.25 (t, J=7.7 Hz, 4H), 3.96-3.85 (m, 2H), 2.35-2.17 (m, 4H), 2.11-1.64 (m, 5H), 1.28-1.23 (m, 1H), 1.06-1.00 (m, 2H), 0.96-0.91 (m, 2H), 0.70-0.66 (m, 2H); MS (ES+) m/z 423.1 (M+1).

Sources & evidence

ORD record
ord-a6f41ff7a3614eb391033683956da87c
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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