3,3-Difluoroazetidine → (1R,2R,4R)-4-[2-Chloro-4-(3,3-difluoro-azetidin-1-yl)-benzenesulfonyl]-2-(3,3-difluoro-azetidine-1-carbonyl)-cyclopentanecarboxylic acid (1-cyano-cyclopropyl)-amide

HRID 1367532Notes

Reaction equation

HRID 1367532 reaction equation
[C:1]([C:3]1([NH:6][C:7]([C@@H:9]2[CH2:13][C@@H:12]([S:14]([C:17]3[CH:22]=[CH:21][C:20](F)=[CH:19][C:18]=3[Cl:24])(=[O:16])=[O:15])[CH2:11][C@H:10]2[C:25]([N:27]2[CH2:30][C:29]([F:32])([F:31])[CH2:28]2)=[O:26])=[O:8])[CH2:5][CH2:4]1)#[N:2].[F:33][C:34]1([F:38])[CH2:37][NH:36][CH2:35]1>>[C:1]([C:3]1([NH:6][C:7]([C@@H:9]2[CH2:13][C@@H:12]([S:14]([C:17]3[CH:22]=[CH:21][C:20]([N:36]4[CH2:37][C:34]([F:38])([F:33])[CH2:35]4)=[CH:19][C:18]=3[Cl:24])(=[O:16])=[O:15])[CH2:11][C@H:10]2[C:25]([N:27]2[CH2:28][C:29]([F:31])([F:32])[CH2:30]2)=[O:26])=[O:8])[CH2:4][CH2:5]1)#[N:2]

Participants

3

Reactant 2

HCID 27582483,3-DifluoroazetidineHCID 59619273(1R,2R,4R)-4-(2-Chloro-4-fluoro-benzenesulfonyl)-2-(3,3-difluoro-azetidine-1-carbonyl)-cyclopentanecarboxylic acid (1-cyano-cyclopropyl)-amide

Product 1

HCID 59619343(1R,2R,4R)-4-[2-Chloro-4-(3,3-difluoro-azetidin-1-yl)-benzenesulfonyl]-2-(3,3-difluoro-azetidine-1-carbonyl)-cyclopentanecarboxylic acid (1-cyano-cyclopropyl)-amide

Procedure

The title compound was prepared in analogy to Example 134 using (1R,2R,4R)-4-(2-Chloro-4-fluoro-benzenesulfonyl)-2-(3,3-difluoro-azetidine-1-carbonyl)-cyclopentanecarboxylic acid (1-cyano-cyclopropyl)-amide (Example 119) and 3,3-difluoroazetidine. Off-white solid. MS (EI): 563.1 (M+H)+.

Sources & evidence

ORD record
ord-f50c4a9444f54140ae9a75fa06ae2b45
Source dataset
uspto-grants-2011_02
Patent number
US07893099B2

Reaction notes

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