4-Cyanobenzoyl chloride → 4-[((2S,4EZ)-4-[(benzyloxy)imino]-2-{[4-(3,4-dichlorophenyl)-1-piperazinyl]-carbonyl}pyrrolidinyl)carbonyl]benzonitrile

HRID 1349037Notes

Reaction equation

HRID 1349037 reaction equation
[CH2:1]([O:8][N:9]=[C:10]1[CH2:14][N:13]([C:15]([O:17]C(C)(C)C)=O)[C@H:12]([C:22]([OH:24])=O)[CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:25]([C:27]1[CH:35]=[CH:34][C:30](C(Cl)=O)=[CH:29][CH:28]=1)#[N:26].[Cl:36][C:37]1[CH:38]=[C:39]([N:44]2[CH2:49][CH2:48][NH:47][CH2:46][CH2:45]2)[CH:40]=[CH:41][C:42]=1[Cl:43]>>[CH2:1]([O:8][N:9]=[C:10]1[CH2:14][N:13]([C:15]([C:30]2[CH:29]=[CH:28][C:27]([C:25]#[N:26])=[CH:35][CH:34]=2)=[O:17])[C@H:12]([C:22]([N:47]2[CH2:46][CH2:45][N:44]([C:39]3[CH:40]=[CH:41][C:42]([Cl:43])=[C:37]([Cl:36])[CH:38]=3)[CH2:49][CH2:48]2)=[O:24])[CH2:11]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 801724-Cyanobenzoyl chlorideHCID 936011-(3,4-Dichlorophenyl)piperazineHCID 131725420(2S,4EZ)-4[(benzyloxy)imino]-1-(tert-butoxycarbonyl)-2-pyrrolidinecarboxylic acid

Product 1

HCID 1317254224-[((2S,4EZ)-4-[(benzyloxy)imino]-2-{[4-(3,4-dichlorophenyl)-1-piperazinyl]-carbonyl}pyrrolidinyl)carbonyl]benzonitrile

Procedure

Following the general method as outlined in Example 22, starting from (2S,4EZ)-4-[(benzyloxy)imino]-1-(tert-butoxycarbonyl)-2-pyrrolidinecarboxylic acid, 4-cyanobenzoyl chloride, and 1-(3,4-dichlorophenyl)piperazine the title compound was obtained in 43% purity by LC/MS. MS(ESI+): m/z=576.6.

Sources & evidence

ORD record
ord-6e15baa21c1b48b7bddb30f3fb695504
Source dataset
uspto-grants-2007_05
Patent number
US07211601B2

Reaction notes

Loading…