N-(azetidin-1-ylsulfonyl)-5-chloro-2-fluoro-4-((1-(trifluoromethyl)-cyclopentyl)methoxy)benzamide → N-(azetidin-1-ylsulfonyl)-5-cyclopropyl-2-fluoro-4-(spiro[2.5]octan-1-ylmethoxy)benzamide

HRID 1849612Notes

Reaction equation

HRID 1849612 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.[N:30]1([S:34]([NH:37][C:38](=[O:57])[C:39]2[CH:44]=[C:43](Cl)[C:42]([O:46][CH2:47][CH:48]3[C:50]4([CH2:55][CH2:54][CH2:53][CH2:52][CH2:51]4)[CH2:49]3)=[CH:41][C:40]=2[F:56])(=[O:36])=[O:35])[CH2:33][CH2:32][CH2:31]1>>[N:30]1([S:34]([NH:37][C:38](=[O:57])[C:39]2[CH:44]=[C:43]([CH:15]3[CH2:10][CH2:9]3)[C:42]([O:46][CH2:47][CH:48]3[C:50]4([CH2:55][CH2:54][CH2:53][CH2:52][CH2:51]4)[CH2:49]3)=[CH:41][C:40]=2[F:56])(=[O:36])=[O:35])[CH2:33][CH2:32][CH2:31]1

Participants

3

Reactant 2

HCID 86703454N-(azetidin-1-ylsulfonyl)-5-chloro-2-fluoro-4-((1-(trifluoromethyl)-cyclopentyl)methoxy)benzamideHCID 86703467N-(azetidin-1-ylsulfonyl)-5-chloro-2-fluoro-4-(spiro[2.5]octan-1-ylmethoxy)benzamide

Product 1

HCID 86703468N-(azetidin-1-ylsulfonyl)-5-cyclopropyl-2-fluoro-4-(spiro[2.5]octan-1-ylmethoxy)benzamide

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 N-(azetidin-1-ylsulfonyl)-5-chloro-2-fluoro-4-(spiro[2.5]octan 1-ylmethoxy)benzamide, the title compound was obtained (0.03 g, 7%) as a colorless solid: 1H NMR (300 MHz, CDCl3) δ 8.67 (br s, 1H), 7.58 (d, J=9.1 Hz, 1H), 6.58 (d, J=14.4 Hz, 1H), 4.24 (t, J=7.7 Hz, 5H), 3.86 (t, J=9.6 Hz, 1H), 2.26 (q, J=7.7 Hz, 2H), 2.15-2.05 (m, 1H), 1.79-1.18 (m, 10H), 1.14-1.04 (m, 1H), 0.96-0.92 (m, 2H), 0.77-0.58 (m, 3H), 0.28 (t, J=5.0 Hz, 1H); MS (ES−) m/z 435.2 (M−1).

Sources & evidence

ORD record
ord-ad4ad8c3be4942f7b09555aa8a13726f
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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