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

HRID 1367570Notes

Reaction equation

HRID 1367570 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[CH2:26][CH2:25][C:24]([F:28])([F:27])[CH2:23]2)=[O:21])[CH2:13]1)(=[O:11])=[O:10].[CH2:29]1[C:31]([NH2:34])([C:32]#[N:33])[CH2:30]1.Cl>>[C:32]([C:31]1([NH:34][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[CH2:26][CH2:25][C:24]([F:28])([F:27])[CH2:23]2)=[O:21])=[O:18])[CH2:29][CH2:30]1)#[N:33]

Participants

3

Reactant 2

HCID 145863631-Amino-1-cyclopropanecarbonitrile hydrochlorideHCID 66918681(1r,2r,4s)-4-(2-Chloro-4-fluoro-benzenesulfonyl)-2-(3,3-difluoro-pyrrolidine-1-carbonyl)-cyclopentanecarboxylic acid

Product 1

HCID 59619283(1R,2R,4R)-4-(2-Chloro-4-fluoro-benzenesulfonyl)-2-(3,3-difluoro-pyrrolidine-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-pyrrolidine-1-carbonyl)-cyclopentanecarboxylic acid (example 186 step 6) and 1-amino-cyclopropyl cyanic hydrochloride. Yellow foam (85%). MS (EI): 504.1 (M+H)+.

Sources & evidence

ORD record
ord-46e6f722361c4b68be2fd79076270d46
Source dataset
uspto-grants-2011_02
Patent number
US07893099B2

Reaction notes

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