Methanesulfonamide → N-(azetidin-1-ylsulfonyl)-4-((1-cyanocyclohexyl)methoxy)-5-cyclopropyl-2-fluorobenzamide

HRID 1849831Notes

Reaction equation

HRID 1849831 reaction equation
[C:1]([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]([OH:21])=O)=[C:17]([F:27])[CH:16]=2)[CH:10]2CC3C[CH:8]([CH2:12][CH:4]1C3)[CH2:9]2)#[N:2].C(C1(COC2C(C3CC3)=CC(C(O)=O)=C(F)C=2)CCCCC1)#N.CS(N)(=O)=O.[N:56]1([S:60]([NH2:63])(=[O:62])=[O:61])[CH2:59][CH2:58][CH2:57]1>>[N:56]1([S:60]([NH:63][C:19](=[O:21])[C:18]2[CH:22]=[C:23]([CH:24]3[CH2:25][CH2:26]3)[C:15]([O:14][CH2:13][C:3]3([C:1]#[N:2])[CH2:4][CH2:12][CH2:8][CH2:9][CH2:10]3)=[CH:16][C:17]=2[F:27])(=[O:62])=[O:61])[CH2:59][CH2:58][CH2:57]1

Participants

5

Reactant 4

HCID 72879MethanesulfonamideHCID 450805661-AzetidinesulfonamideHCID 867036554-((2-Cyanoadamantan-2-yl)methoxy)-5-cyclopropyl-2-fluorobenzoic acidHCID 867037174-((1-Cyanocyclohexyl)methoxy)-5-cyclopropyl-2-fluorobenzoic acid

Product 1

HCID 86703719N-(azetidin-1-ylsulfonyl)-4-((1-cyanocyclohexyl)methoxy)-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-((1-cyanocyclohexyl)methoxy)-5-cyclopropyl-2-fluorobenzoic acid and to replace methanesulfonamide with azetidine-1-sulfonamide, the title compound was obtained as a colorless solid (0.061 g, 42%): 1H NMR (300 MHz, DMSO-d6) δ 11.65 (br s, 1H), 7.14 (d, J=8.1 Hz, 1H), 6.99 (d, J=12.6 Hz, 1H), 4.15 (s, 2H), 4.02 (t, J=7.6, 7.6 Hz, 4H), 2.18-2.08 (m, 2H), 2.03-1.97 (m, 3H), 1.73-1.66 (m, 3H), 1.51-1.39 (m, 4H), 1.20 (br s, 1H), 0.91-0.85 (m, 2H), 0.69-0.64 (m, 2H); 19F NMR (282 MHz, DMSO-d6) δ −112.6 (s, 1F); MS (ES−) m/z 434.1 (M−1).

Sources & evidence

ORD record
ord-f65d0bbd09b44c35a7bf2c4626ad236e
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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