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

HRID 1849787Notes

Reaction equation

CS(N)(=O)=O.[N:6]1([S:10]([NH2:13])(=[O:12])=[O:11])[CH2:9][CH2:8][CH2:7]1.[C:14]12([CH2:21][O:22][C:23]3[C:31]([CH:32]4[CH2:34][CH2:33]4)=[CH:30][C:26]([C:27](O)=[O:28])=[C:25]([F:35])[CH:24]=3)[CH2:20][CH:19]1[CH2:18][CH2:17][CH2:16][CH2:15]2>>[N:6]1([S:10]([NH:13][C:27](=[O:28])[C:26]2[CH:30]=[C:31]([CH:32]3[CH2:33][CH2:34]3)[C:23]([O:22][CH2:21][C:14]34[CH2:20][CH:19]3[CH2:18][CH2:17][CH2:16][CH2:15]4)=[CH:24][C:25]=2[F:35])(=[O:12])=[O:11])[CH2:9][CH2:8][CH2:7]1

Participants

Reactant 3

HCID 72879Methanesulfonamide

HCID 450805661-Azetidinesulfonamide

HCID 867036674-(Bicyclo[4.1.0]heptan-1-ylmethoxy)-5-cyclopropyl-2-fluorobenzoic acid

Product 1

HCID 86703669N-(azetidin-1-ylsulfonyl)-4-(bicyclo[4.1.0]heptan-1-ylmethoxy)-5-cyclopropyl-2-fluorobenzamide

Procedure

Following the procedure as described in Example 332 Step 7 and making non-critical variations to replace methanesulfonamide with azetidine-1-sulfonamide and to replace 4-(((1r,3r,5r,7r)-2-cyanoadamantan-2-yl)methoxy)-5-cyclopropyl-2-fluorobenzoic acid with 4-(bicyclo[4.1.0]heptan-1-ylmethoxy)-5-cyclopropyl-2-fluorobenzoic acid, the title compound was obtained following purification by reverse-phase HPLC as a colorless powder (0.037 g, 37%): 1H NMR (300 MHz, DMSO-d6) δ 11.60 (br, s, 1H), 7.15 (d, J=8.3 Hz, 1H), 6.87 (d, J=13.0 Hz, 1H), 4.09-3.98 (m, 4H), 3.92-3.84 (m, 1H), 3.80-3.74 (m, 1H), 2.23-1.98 (m, 3H), 1.96-1.68 (m, 3H), 1.66-1.52 (m, 1H), 1.34-1.13 (m, 4H), 1.04-0.83 (m, 3H), 0.75-0.60 (m, 3H), 0.41-0.33 (m, 1H); MS (ES+) m/z 423.1 (M+1)

Sources & evidence

ORD record: ord-a83a4db1f7c94045964cdb1ad3d33d14
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08952169B2

Reaction notes

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