O-Phenylenediamine → 4-{[(2S,4EZ)-2-(1H-benzimidazol-2-yl)-4-(cyanomethylene)pyrrolidinyl]-carbonyl}benzonitrile

HRID 1349109Notes

Reaction equation

HRID 1349109 reaction equation
C(O[C:6]([N:8]1[CH2:12][C:11](=[CH:13][C:14]#[N:15])[CH2:10][C@H:9]1[C:16](O)=O)=[O:7])(C)(C)C.[C:19]([C:21]1[CH:29]=[CH:28][C:24](C(Cl)=O)=[CH:23][CH:22]=1)#[N:20].[C:30]1([NH2:37])[C:31]([NH2:36])=[CH:32][CH:33]=[CH:34][CH:35]=1>>[NH:36]1[C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=2[N:37]=[C:16]1[C@@H:9]1[CH2:10][C:11](=[CH:13][C:14]#[N:15])[CH2:12][N:8]1[C:6]([C:24]1[CH:23]=[CH:22][C:21]([C:19]#[N:20])=[CH:29][CH:28]=1)=[O:7]

Participants

4

Reactant 3

HCID 7243O-PhenylenediamineHCID 801724-Cyanobenzoyl chlorideHCID 69250314(2S,4EZ)-1-(tertbutoxycarbonyl)-4-(cyanomethylene)-2-pyrrolidinecarboxylic acid

Product 1

HCID 692478784-{[(2S,4EZ)-2-(1H-benzimidazol-2-yl)-4-(cyanomethylene)pyrrolidinyl]-carbonyl}benzonitrile

Procedure

Following the general method as outlined in Example 22, starting from (2S,4EZ)-1-(tert-butoxycarbonyl)-4-(cyanomethylene)-2-pyrrolidinecarboxylic acid, 4-cyanobenzoyl chloride, and 1,2-benzenediamine the title compound was obtained in 84% purity by LC/MS. MS(ESI+): m/z=354.2.

Sources & evidence

ORD record
ord-0e74bfacbc064b35adf555294952edb6
Source dataset
uspto-grants-2007_05
Patent number
US07211601B2

Reaction notes

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