Methanesulfonamide → N-(azetidin-1-ylsulfonyl)-5-cyclopropyl-2-fluoro-4-((1-fluorocyclohexyl)methoxy)benzamide

HRID 1849798Notes

Reaction equation

HRID 1849798 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][CH2:55][C:56]3([F:62])[CH2:61][CH2:60][CH2:59][CH2:58][CH2:57]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][CH2:55][C:56]3([F:62])[CH2:57][CH2:58][CH2:59][CH2:60][CH2:61]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 867036815-Cyclopropyl-2-fluoro-4-((1-fluorocyclohexyl)methoxy)benzoic acid

Product 1

HCID 86703682N-(azetidin-1-ylsulfonyl)-5-cyclopropyl-2-fluoro-4-((1-fluorocyclohexyl)methoxy)benzamide

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-2-fluoro-4-((1-fluorocyclohexyl)methoxy)benzoic 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) 11.64 (br s, 1H), 7.15 (d, J=8.3 Hz, 1H), 7.02 (d, J=8.3 Hz, 1H), 4.16 (d, J=8.3 Hz, 2H), 4.05 (dd, J=8.3, 4H), 2.25-1.82 (m, 5H), 1.78-1.45 (m, 7H), 1.41-1.21 (m, 1H), 0.96-0.86 (m, 2H), 0.75-0.63 (m, 2H); MS (ES+) m/z 429.1 (M+1)

Sources & evidence

ORD record
ord-6877e2e67cfd4352922d7a29fbd2eb21
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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