1-Amino-1-cyclopropanecarbonitrile hydrochloride → (1R,2R,4R)-4-(2-Chloro-4-fluoro-benzenesulfonyl)-2-(3,3-difluoro-azetidine-1-carbonyl)-cyclopentanecarboxylic acid (1-cyano-cyclopropyl)-amide

HRID 1367519Notes

Reaction equation

HRID 1367519 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[S:9]([C@@H:12]1[CH2:16][C@@H:15]([C:17](O)=[O:18])[C@H:14]([C:20]([N:22]2[CH2:25][C:24]([F:27])([F:26])[CH2:23]2)=[O:21])[CH2:13]1)(=[O:11])=[O:10].[CH2:28]1[C:30]([NH2:33])([C:31]#[N:32])[CH2:29]1.Cl>>[C:31]([C:30]1([NH:33][C:17]([C@@H:15]2[CH2:16][C@@H:12]([S:9]([C:3]3[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=3[Cl:1])(=[O:11])=[O:10])[CH2:13][C@H:14]2[C:20]([N:22]2[CH2:23][C:24]([F:27])([F:26])[CH2:25]2)=[O:21])=[O:18])[CH2:28][CH2:29]1)#[N:32]

Participants

3

Reactant 2

HCID 145863631-Amino-1-cyclopropanecarbonitrile hydrochlorideHCID 66918865(1r,2r,4s)-4-(2-Chloro-4-fluoro-benzenesulfonyl)-2-(3,3-difluoro-azetidine-1-carbonyl)-cyclopentanecarboxylic acid

Product 1

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

Procedure

The title compound was prepared in analogy to Example 117, step 7, using (1R,2R,4S)-4-(2-Chloro-4-fluoro-benzenesulfonyl)-2-(3,3-difluoro-azetidine-1-carbonyl)-cyclopentanecarboxylic acid and 1-amino-cyclopropyl cyanic hydrochloride. Off-white solid. MS (EI): 490.1 (M+H)+.

Sources & evidence

ORD record
ord-88c5dd0b37034af9b10f172b4cda119c
Source dataset
uspto-grants-2011_02
Patent number
US07893099B2

Reaction notes

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