N-(azetidin-1-ylsulfonyl)-5-chloro-2-fluoro-4-((1-(trifluoromethyl)-cyclopentyl)methoxy)benzamide → HCID 178505174, compound

HRID 1849601Notes

Reaction equation

HRID 1849601 reaction equation
N1(S(N[C:9](=O)[C:10]2[CH:15]=C(Cl)C(OCC3(C(F)(F)F)CCCC3)=CC=2F)(=O)=O)CCC1.Cl[C:31]1[C:32]([O:45][C@H:46]2[CH2:51][CH2:50][C@H:49]([C:52]([F:55])([F:54])[F:53])[CH2:48][CH2:47]2)=[CH:33][C:34]([F:44])=[C:35]([CH:43]=1)[C:36]([NH:38][S:39]([CH3:42])(=[O:41])=[O:40])=[O:37]>>[CH:15]1([C:31]2[C:32]([O:45][C@H:46]3[CH2:51][CH2:50][C@H:49]([C:52]([F:55])([F:54])[F:53])[CH2:48][CH2:47]3)=[CH:33][C:34]([F:44])=[C:35]([CH:43]=2)[C:36]([NH:38][S:39]([CH3:42])(=[O:41])=[O:40])=[O:37])[CH2:10][CH2:9]1

Participants

3

Reactant 2

HCID 86703454N-(azetidin-1-ylsulfonyl)-5-chloro-2-fluoro-4-((1-(trifluoromethyl)-cyclopentyl)methoxy)benzamideHCID 178505177HCID 178505177, compound

Product 1

HCID 178505174HCID 178505174, compound

Procedure

Following the procedure as described in Example 165 and making variations as required to replace N-(azetidin-1-ylsulfonyl)-5-chloro-2-fluoro-4-((1-(trifluoromethyl)-cyclopentyl)methoxy)benzamide with 5-chloro-2-fluoro-N-(methylsulfonyl)-4-((trans-4-(trifluoromethyl)cyclohexyl)oxy)benzamide, the title compound was obtained (0.24 g, 57%) as a colorless solid: 1H NMR (300 MHz, CDCl3) δ 8.68 (d, J=16.2 Hz, 1H), 7.61 (d, J=9.0 Hz, 1H), 6.55 (d, J=14.7 Hz, 1H), 4.69-4.65 (m, 1H), 3.39 (s, 3H), 2.24-1.95 (m, 4H), 1.83-1.55 (m, 6H), 0.97-0.89 (m, 2H), 0.66-0.60 (m, 2H); MS (ES−) m/z 422.2 (M−1); MS (ES+) m/z 424.1 (M+1).

Sources & evidence

ORD record
ord-b42047e10ce8450593996c30a0ef654b
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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