O-Phenylenediamine → (2EZ)-[5-(1H-benzimidazol-2-yl)-1-([1,1'-biphenyl]-4-ylcarbonyl)-3-pyrrolidinylidene]ethanenitrile

HRID 1349104Notes

Reaction equation

HRID 1349104 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]1([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:24]=[CH:23][C:22](C(Cl)=O)=[CH:21][CH:20]=1.[C:34]1([NH2:41])[C:35]([NH2:40])=[CH:36][CH:37]=[CH:38][CH:39]=1>>[NH:40]1[C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][C:34]=2[N:41]=[C:16]1[CH:9]1[N:8]([C:6]([C:31]2[CH:30]=[CH:29][C:28]([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)=[CH:33][CH:32]=2)=[O:7])[CH2:12][C:11](=[CH:13][C:14]#[N:15])[CH2:10]1

Participants

4

Reactant 3

HCID 7243O-PhenylenediamineHCID 841514-Phenylbenzoyl chlorideHCID 69250314(2S,4EZ)-1-(tertbutoxycarbonyl)-4-(cyanomethylene)-2-pyrrolidinecarboxylic acid

Product 1

HCID 69250189(2EZ)-[5-(1H-benzimidazol-2-yl)-1-([1,1'-biphenyl]-4-ylcarbonyl)-3-pyrrolidinylidene]ethanenitrile

Procedure

Following the general method as outlined in Example 22, starting from (2S,4EZ)-1-(tert-butoxycarbonyl)-4-(cyanomethylene)-2-pyrrolidinecarboxylic acid, [1,1′-biphenyl]-4-carbonyl chloride, and 1,2-benzenediamine the title compound was obtained in 70% purity by LC/MS. MS(ESI+): m/z=405.2.

Sources & evidence

ORD record
ord-9e29f46cb3d24781b97e3e8c87a9199d
Source dataset
uspto-grants-2007_05
Patent number
US07211601B2

Reaction notes

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