Methanesulfonamide → N-(azetidin-1-ylsulfonyl)-5-chloro-4-((4,4-difluorocyclohexyl)oxy)-2-fluorobenzamide

HRID 1849822Notes

Reaction equation

HRID 1849822 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.[Cl:41][C:42]1[C:43]([O:52][CH:53]2[CH2:58][CH2:57][C:56]([F:60])([F:59])[CH2:55][CH2:54]2)=[CH:44][C:45]([F:51])=[C:46]([CH:50]=1)[C:47](O)=[O:48]>>[N:6]1([S:10]([NH:13][C:47](=[O:48])[C:46]2[CH:50]=[C:42]([Cl:41])[C:43]([O:52][CH:53]3[CH2:58][CH2:57][C:56]([F:60])([F:59])[CH2:55][CH2:54]3)=[CH:44][C:45]=2[F:51])(=[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 867036885-Chloro-4-((4,4-difluorocyclohexyl)oxy)-2-fluorobenzoic acid

Product 1

HCID 86703710N-(azetidin-1-ylsulfonyl)-5-chloro-4-((4,4-difluorocyclohexyl)oxy)-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-((2-cyanoadamantan-2-yl)methoxy)-5-cyclopropyl-2-fluorobenzoic acid with 5-chloro-4-((4,4-difluorocyclohexyl)oxy)-2-fluorobenzoic acid, the title compound was obtained as a colorless solid (0.028 g, 19%): 1H NMR (300 MHz, DMSO-d6) δ 11.80 (br s, 1H), 7.78 (d, J=7.5 Hz, 1H), 7.38 (d, J=12.4 Hz, 1H), 4.85 (br s, 1H), 4.00 (t, J=7.7, 7.7 Hz, 4H), 2.18-1.86 (m, 10H); 19F NMR (282 MHz, DMSO-d6) δ −92.2 (d, J=231 Hz, 1F), −98.5 (d, J=231 Hz, 1F), −110.1 (s, 1F); MS (ES−) m/z 425.1, 427.1 (M−1).

Sources & evidence

ORD record
ord-17efd120739e40218f804eb03973925d
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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