N-(azetidin-1-ylsulfonyl)-5-chloro-2-fluoro-4-((1-(trifluoromethyl)-cyclopentyl)methoxy)benzamide → 5-cyclopropyl-2-fluoro-N-(methylsulfonyl)-4-((1-(trifluoromethyl)-cyclopropyl)methoxy)benzamide

HRID 1849608Notes

Reaction equation

HRID 1849608 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][CH2:46][C:47]2([C:50]([F:53])([F:52])[F:51])[CH2:49][CH2:48]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][CH2:46][C:47]3([C:50]([F:53])([F:52])[F:51])[CH2:49][CH2:48]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 867034645-chloro-2-fluoro-N-(methylsulfonyl)-4-((1-(trifluoromethyl)-cyclopropyl)-methoxy)benzamide

Product 1

HCID 867034635-cyclopropyl-2-fluoro-N-(methylsulfonyl)-4-((1-(trifluoromethyl)-cyclopropyl)methoxy)benzamideYield 19%

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-((1-(trifluoromethyl)-cyclopropyl)-methoxy)benzamide. Purification by reverse-phase preparative HPLC to yield the title compound (0.047 g, 19%): 1H NMR (300 MHz, DMSO-d6) 11.94 (br s, 1H), 7.14 (d, J=8.3 Hz, 1H), 6.96 (d, J=12.9 Hz, 1H), 4.23 (s, 2H), 3.31 (s, 3H), 2.09-2.00 (m, 1H), 1.16-1.11 (m, 2H), 1.07-1.02 (m, 2H), 0.93-0.86 (m, 2H), 0.72-0.66 (m, 2H); MS (ES−) m/z 394.1 (M−1).

Workup

  1. customPurification by reverse-phase preparative HPLC

Sources & evidence

ORD record
ord-76eea746dd6f41e3aa2eab7ee05417c0
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

Loading…