N-Methyl-o-phenylenediamine → (3Ez,5s)-5-(1-methyl-1h-benzimidazol-2-yl)-1-[(2'-methyl[1,1'-biphenyl]-4-yl)carbonyl]-3-pyrrolidinone o-methyloxime

HRID 1349023Notes

Reaction equation

HRID 1349023 reaction equation
C(O[C:6]([N:8]1[CH2:12][C:11](=[N:13][O:14][CH3:15])[CH2:10][C@H:9]1[C:16](O)=O)=[O:7])(C)(C)C.[CH3:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[C:26]1[CH:31]=[CH:30][C:29](C(O)=O)=[CH:28][CH:27]=1.[CH3:35][NH:36][C:37]1[C:38]([NH2:43])=[CH:39][CH:40]=[CH:41][CH:42]=1>>[CH3:15][O:14][N:13]=[C:11]1[CH2:10][C@@H:9]([C:16]2[N:36]([CH3:35])[C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=3[N:43]=2)[N:8]([C:6]([C:29]2[CH:28]=[CH:27][C:26]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=3[CH3:19])=[CH:31][CH:30]=2)=[O:7])[CH2:12]1

Participants

4

Reactant 3

HCID 78498N-Methyl-o-phenylenediamineHCID 27598152'-Methyl-biphenyl-4-carboxylic acidHCID 58714586(2S,4EZ)-1(tert-butoxycarbonyl)-4-(methoxyimino)-2-pyrrolidinecarboxylic acid

Product 1

HCID 131725407(3Ez,5s)-5-(1-methyl-1h-benzimidazol-2-yl)-1-[(2'-methyl[1,1'-biphenyl]-4-yl)carbonyl]-3-pyrrolidinone o-methyloxime

Procedure

Following the general method as outlined in Example 11, starting from (2S,4EZ)-1-(tert-butoxycarbonyl)-4-(methoxyimino)-2-pyrrolidinecarboxylic acid, 2′-methyl[1,1′-biphenyl]-4-carboxylic acid, and N1-methyl-1,2-benzenediamine, the title compound was obtained in 83% purity by HPLC. MS(ESI+): m/z=439.

Sources & evidence

ORD record
ord-01e02ce1209d460fbf58851e093ec483
Source dataset
uspto-grants-2007_05
Patent number
US07211601B2

Reaction notes

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