Methanesulfonamide → 5-cyclopropyl-N-(cyclopropylsulfonyl)-4-((3,3-dimethyl-cyclohexyl)oxy)-2-fluorobenzamide

HRID 1849810Notes

Reaction equation

HRID 1849810 reaction equation
CS(N)(=O)=O.[CH:6]1([S:9]([NH2:12])(=[O:11])=[O:10])[CH2:8][CH2:7]1.C(C1(COC2C(C3CC3)=CC(C(O)=O)=C(F)C=2)C2CC3CC(CC1C3)C2)#N.[CH:40]1([C:43]2[C:44]([O:53][CH:54]3[CH2:59][CH2:58][CH2:57][C:56]([CH3:61])([CH3:60])[CH2:55]3)=[CH:45][C:46]([F:52])=[C:47]([CH:51]=2)[C:48](O)=[O:49])[CH2:42][CH2:41]1>>[CH:40]1([C:43]2[C:44]([O:53][CH:54]3[CH2:59][CH2:58][CH2:57][C:56]([CH3:61])([CH3:60])[CH2:55]3)=[CH:45][C:46]([F:52])=[C:47]([CH:51]=2)[C:48]([NH:12][S:9]([CH:6]2[CH2:8][CH2:7]2)(=[O:11])=[O:10])=[O:49])[CH2:42][CH2:41]1

Participants

5

Reactant 4

HCID 72879MethanesulfonamideHCID 15765418CyclopropanesulfonamideHCID 867036554-((2-Cyanoadamantan-2-yl)methoxy)-5-cyclopropyl-2-fluorobenzoic acidHCID 867036935-Cyclopropyl-4-((3,3-dimethylcyclohexyl)oxy)-2-fluorobenzoic acid

Product 1

HCID 867036955-cyclopropyl-N-(cyclopropylsulfonyl)-4-((3,3-dimethyl-cyclohexyl)oxy)-2-fluorobenzamide

Procedure

Following the procedure as described in Example 332 Step 7 and making non-critical variations to replace methane sulfonamide with cyclopropane 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 (0.07 g, 31%): 1H NMR (300 MHz, DMSO-d6) δ11.79 (s, 1H), 7.10 (d, J=8.5 Hz, 1H), 7.03 (d, J=13.3 Hz, 1H), 4.67-4.58 (m, 1H), 3.11-3.03 (m, 1H), 2.06-1.95 (m, 2H), 1.76-1.70 (m, 1H), 1.65-1.54 (m, 2H), 1.37-1.17 (m, 4H), 1.13-1.08 (m, 4H), 0.98 (s, 3H), 0.97 (s, 3H), 0.90-0.84 (m, 2H), 0.68-0.63 (m, 2H); MS (ES+) m/z 410.0 (M+1).

Sources & evidence

ORD record
ord-89be39bbdbbb40869829c9cd8b5e2ddd
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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