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

HRID 239861Notes

Reaction equation

HRID 239861 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](O)=[O:31])[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][C@H: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[F:44]>>[C:45]([CH:34]([NH:33][C:30](=[O:31])[C@@H:24]([NH:23][C@@H:18]([C:15]1[CH:16]=[CH:17][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:13][CH:14]=1)[C:19]([F:22])([F:21])[F:20])[CH2:25][C:26]([F:29])([CH3:27])[CH3:28])[CH2:35][C:36]1[CH:43]=[CH:42][C:39]([C:40]#[N:41])=[CH:38][C:37]=1[F:44])#[N:46]

Participants

3

Reactant 2

HCID 684437434-[(2S)-(2-amino-2-cyanoethyl)]-3-fluorobenzonitrileHCID 68444063N-{(1S)-1-[2'-chloro-4'-(methylsulfonyl)biphenyl-4-yl]-2,2,2-trifluoroethyl}-4-fluoro-L-leucine

Product 1

HCID 42633147(S)-2-[(S)-1-(2'-Chloro-4'-methanesulfonyl-biphenyl-4-yl)-2,2,2-trifluoro-ethylamino]-4-fluoro-4-methyl-pentanoic acid [1-cyano-2-(4-cyano-2-fluoro-phenyl)-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 [1-cyano-2-(4-cyano-2-fluoro-phenyl)-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-[(2S)-(2-amino-2-cyanoethyl)]-3-fluorobenzonitrile using procedure described in Example 6.

Sources & evidence

ORD record
ord-156c83722fb242b8847d1519f2f4bc77
Source dataset
uspto-grants-2014_02
Patent number
US08642799B2

Reaction notes

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