3-Amino-9-ethylcarbazole → (2S, 4EZ)-4-(cyanomethylene)-N-(9-ethyl-9H-carbazol-3yl)-1-(4-phenoxybenzoyl)-2-pyrrolidinecarboxamide

HRID 1349115Notes

Reaction equation

HRID 1349115 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]([OH:18])=O)=[O:7])(C)(C)C.[O:19]([C:26]1[CH:34]=[CH:33][C:29](C(Cl)=O)=[CH:28][CH:27]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[CH2:35]([N:37]1[C:49]2[CH:48]=[CH:47][C:46]([NH2:50])=[CH:45][C:44]=2[C:43]2[C:38]1=[CH:39][CH:40]=[CH:41][CH:42]=2)[CH3:36]>>[C:14]([CH:13]=[C:11]1[CH2:12][N:8]([C:6](=[O:7])[C:29]2[CH:28]=[CH:27][C:26]([O:19][C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)=[CH:34][CH:33]=2)[C@H:9]([C:16]([NH:50][C:46]2[CH:47]=[CH:48][C:49]3[N:37]([CH2:35][CH3:36])[C:38]4[C:43]([C:44]=3[CH:45]=2)=[CH:42][CH:41]=[CH:40][CH:39]=4)=[O:18])[CH2:10]1)#[N:15]

Participants

4

Reactant 3

HCID 85883-Amino-9-ethylcarbazoleHCID 741934-Phenoxybenzoyl chlorideHCID 69250314(2S,4EZ)-1-(tertbutoxycarbonyl)-4-(cyanomethylene)-2-pyrrolidinecarboxylic acid

Product 1

HCID 69250533(2S, 4EZ)-4-(cyanomethylene)-N-(9-ethyl-9H-carbazol-3yl)-1-(4-phenoxybenzoyl)-2-pyrrolidinecarboxamide

Procedure

Following the general method as outlined in Example 22, starting from (2S,4EZ)-1-(tert-butoxycarbonyl)-4-(cyanomethylene)-2-pyrrolidinecarboxylic acid, 4-phenoxybenzoyl chloride, and 9-ethyl-9H-carbazol-3-amine the title compound was obtained in 37% purity by LC/MS. MS(ESI+): m/z=541.4.

Sources & evidence

ORD record
ord-255122a39ed74f4db9d915b67f0ae5b4
Source dataset
uspto-grants-2007_05
Patent number
US07211601B2

Reaction notes

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