4-((adamantan-2-yloxy)methyl)-5-chloro-2-fluoro-N-(methylsulfonyl)benzamide → N-(azetidin-1-ylsulfonyl)-5-cyclopropyl-2-fluoro-4-(spiro[2.5]octan-6-ylmethoxy)benzamide

HRID 1849650Notes

Reaction equation

HRID 1849650 reaction equation
[CH:1]12[CH2:10]C3CC(CC(C3)[CH:2]1OCC1C(Cl)=CC(C(NS(C)(=O)=O)=O)=C(F)C=1)C2.[N:28]1([S:32]([NH:35][C:36](=[O:55])[C:37]2[CH:42]=[C:41](Cl)[C:40]([O:44][CH2:45][CH:46]3[CH2:53][CH2:52][C:49]4([CH2:51][CH2:50]4)[CH2:48][CH2:47]3)=[CH:39][C:38]=2[F:54])(=[O:34])=[O:33])[CH2:31][CH2:30][CH2:29]1>>[N:28]1([S:32]([NH:35][C:36](=[O:55])[C:37]2[CH:42]=[C:41]([CH:10]3[CH2:1][CH2:2]3)[C:40]([O:44][CH2:45][CH:46]3[CH2:53][CH2:52][C:49]4([CH2:51][CH2:50]4)[CH2:48][CH2:47]3)=[CH:39][C:38]=2[F:54])(=[O:34])=[O:33])[CH2:31][CH2:30][CH2:29]1

Participants

3

Reactant 2

HCID 867028574-((adamantan-2-yloxy)methyl)-5-chloro-2-fluoro-N-(methylsulfonyl)benzamideHCID 86703512N-(azetidin-1-ylsulfonyl)-5-chloro-2-fluoro-4-(spiro[2.5]octan-6-ylmethoxy)benzamide

Product 1

HCID 86703513N-(azetidin-1-ylsulfonyl)-5-cyclopropyl-2-fluoro-4-(spiro[2.5]octan-6-ylmethoxy)benzamide

Procedure

Following the procedure as described in Example 49 and making variations as required to replace 4-((adamantan-2-yloxy)methyl)-5-chloro-2-fluoro- N-(methylsulfonyl)benzamide with N-(azetidin-1-ylsulfonyl)-5-chloro-2-fluoro-4-(spiro[2.5]octan-6-ylmethoxy)benzamide, the title compound was obtained as a colorless solid (0.39 g, 66%): 1H NMR (300 MHz, CDCl3) δ 8.74-8.59 (m, 1H), 7.64-7.54 (m, 1H), 6.64-6.52 (m, 1H), 4.31-4.18 (m, 4H), 3.93-3.81 (m, 2H), 2.35-2.20 (m, 2H), 2.13-2.00 (m, 1H), 1.99-1.72 (m, 5H), 1.40-1.20 (m, 2H), 1.02-0.85 (m, 4H), 0.73-0.61 (m, 2H), 0.37-0.14 (m, 4H); MS (ES+1) m/z 437.2 (M+1).

Sources & evidence

ORD record
ord-f933d9bdd28b428ba8e25f9264d6616b
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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