Methanesulfonamide → N-(azetidin-1-ylsulfonyl)-5-cyclopropyl-4-((3,3-dimethylcyclohexyl)oxy)-2-fluorobenzamide

HRID 1849809Notes

Reaction equation

HRID 1849809 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(C1(COC2C(C3CC3)=CC(C(O)=O)=C(F)C=2)C2CC3CC(CC1C3)C2)#N.[CH:41]1([C:44]2[C:45]([O:54][CH:55]3[CH2:60][CH2:59][CH2:58][C:57]([CH3:62])([CH3:61])[CH2:56]3)=[CH:46][C:47]([F:53])=[C:48]([CH:52]=2)[C:49](O)=[O:50])[CH2:43][CH2:42]1>>[N:6]1([S:10]([NH:13][C:49](=[O:50])[C:48]2[CH:52]=[C:44]([CH:41]3[CH2:42][CH2:43]3)[C:45]([O:54][CH:55]3[CH2:60][CH2:59][CH2:58][C:57]([CH3:62])([CH3:61])[CH2:56]3)=[CH:46][C:47]=2[F:53])(=[O:12])=[O:11])[CH2:9][CH2:8][CH2:7]1

Participants

5

Reactant 4

HCID 72879MethanesulfonamideHCID 450805661-AzetidinesulfonamideHCID 867036554-((2-Cyanoadamantan-2-yl)methoxy)-5-cyclopropyl-2-fluorobenzoic acidHCID 867036935-Cyclopropyl-4-((3,3-dimethylcyclohexyl)oxy)-2-fluorobenzoic acid

Product 1

HCID 86703694N-(azetidin-1-ylsulfonyl)-5-cyclopropyl-4-((3,3-dimethylcyclohexyl)oxy)-2-fluorobenzamide

Procedure

Following the procedure as described in Example 332 Step 7 and making non-critical variations to replace methane sulfonamide with azetidine-1-sulfonamide and to replace 4-((2-cyanoadamantan-2-yl)methoxy)-5-cyclopropyl-2-fluorobenzoic acid with 5-cyclopropyl-4-((3,3-dimethylcyclohexyl)oxy)-2-fluorobenzoic acid, the title compound was obtained as a white solid (0.035 g, 15%): 1H NMR (300 MHz, DMSO-d6) δ11.58 (s, 1H), 7.11 (d, J=8.5 Hz, 1H), 7.03 (d, J=13.3 Hz, 1H), 4.67-4.58 (m, 1H), 4.04 (t, J=7.7 Hz, 4H), 2.21-2.11 (m, 2H), 2.06-1.96 (m, 2H), 1.76-1.70 (m, 1H), 1.65-1.53 (m, 2H), 1.38-1.14 (m, 4H), 0.98 (s, 3H), 0.97 (s, 3H), 0.90-0.84 (m, 2H), 0.69-0.64 (m, 2H); MS (ES+) m/z 425.1 (M+1).

Sources & evidence

ORD record
ord-fe50f4a87eda4eb39ef65331cc4c2575
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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