4-(2-Amino-2-cyanoethyl)-3-chlorobenzonitrile → (S)-2-[(S)-1-(2'-Chloro-4'-methanesulfonyl-biphenyl-4-yl)-2,2,2-trifluoro-ethylamino]-4-fluoro-4-methyl-pentanoic acid [2-(2-chloro-4-cyano-phenyl)-1-cyano-ethyl]-amide

HRID 239860Notes

Reaction equation

HRID 239860 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([S:8]([CH3:11])(=[O:10])=[O:9])[CH:5]=[CH:4][C:3]=1[C:12]1[CH:17]=[CH:16][C:15]([C@H:18]([NH:23][C@H:24]([C:30]([OH:32])=O)[CH2:25][C:26]([F:29])([CH3:28])[CH3:27])[C:19]([F:22])([F:21])[F:20])=[CH:14][CH:13]=1.[NH2:33][CH:34]([C:45]#[N:46])[CH2:35][C:36]1[CH:43]=[CH:42][C:39]([C:40]#[N:41])=[CH:38][C:37]=1[Cl:44]>>[Cl:44][C:37]1[CH:38]=[C:39]([C:40]#[N:41])[CH:42]=[CH:43][C:36]=1[CH2:35][CH:34]([NH:33][C:30](=[O:32])[C@@H:24]([NH:23][C@@H:18]([C:15]1[CH:14]=[CH:13][C:12]([C:3]2[CH:4]=[CH:5][C:6]([S:8]([CH3:11])(=[O:10])=[O:9])=[CH:7][C:2]=2[Cl:1])=[CH:17][CH:16]=1)[C:19]([F:21])([F:20])[F:22])[CH2:25][C:26]([F:29])([CH3:28])[CH3:27])[C:45]#[N:46]

Participants

3

Reactant 2

HCID 684432854-(2-Amino-2-cyanoethyl)-3-chlorobenzonitrileHCID 68444063N-{(1S)-1-[2'-chloro-4'-(methylsulfonyl)biphenyl-4-yl]-2,2,2-trifluoroethyl}-4-fluoro-L-leucine

Product 1

HCID 42633148(S)-2-[(S)-1-(2'-Chloro-4'-methanesulfonyl-biphenyl-4-yl)-2,2,2-trifluoro-ethylamino]-4-fluoro-4-methyl-pentanoic acid [2-(2-chloro-4-cyano-phenyl)-1-cyano-ethyl]-amide

Procedure

(S)-2-[(S)-1-(2′-Chloro-4′-methanesulfonyl-biphenyl-4-yl)-2,2,2-trifluoro-ethylamino]-4-fluoro-4-methyl-pentanoic acid [2-(2-chloro-4-cyano-phenyl)-1-cyano-ethyl]-amide was prepared from N-{(1S)-1-[2′-chloro-4′-(methylsulfonyl)biphenyl-4-yl]-2,2,2-trifluoroethyl}-4-fluoro-L-leucine and 4-(2-amino-2-cyanoethyl)-3-chlorobenzonitrile by following procedures as in step 4 of Example 2.

Sources & evidence

ORD record
ord-0bf7d9dd0946485babcc200344a9dd54
Source dataset
uspto-grants-2014_02
Patent number
US08642799B2

Reaction notes

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