3-Amino-9-ethylcarbazole → (2S,4EZ)-1-([1,1'-biphenyl]-4-ylcarbonyl)-4-(cyanomethylene)-N-(9-ethyl-9H-carbazol-3-yl)-2-pyrrolidinecarboxamide

HRID 1349119Notes

Reaction equation

HRID 1349119 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.[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.[CH2:34]([N:36]1[C:48]2[CH:47]=[CH:46][C:45]([NH2:49])=[CH:44][C:43]=2[C:42]2[C:37]1=[CH:38][CH:39]=[CH:40][CH:41]=2)[CH3:35]>>[C:28]1([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:29]=[CH:30][C:31]([C:6]([N:8]2[CH2:12][C:11](=[CH:13][C:14]#[N:15])[CH2:10][C@H:9]2[C:16]([NH:49][C:45]2[CH:46]=[CH:47][C:48]3[N:36]([CH2:34][CH3:35])[C:37]4[C:42]([C:43]=3[CH:44]=2)=[CH:41][CH:40]=[CH:39][CH:38]=4)=[O:18])=[O:7])=[CH:32][CH:33]=1

Participants

4

Reactant 3

HCID 85883-Amino-9-ethylcarbazoleHCID 841514-Phenylbenzoyl chlorideHCID 69250314(2S,4EZ)-1-(tertbutoxycarbonyl)-4-(cyanomethylene)-2-pyrrolidinecarboxylic acid

Product 1

HCID 69249541(2S,4EZ)-1-([1,1'-biphenyl]-4-ylcarbonyl)-4-(cyanomethylene)-N-(9-ethyl-9H-carbazol-3-yl)-2-pyrrolidinecarboxamide

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 9-ethyl-9H-carbazol-3-amine the title compound was obtained in 32% purity by LC/MS. MS(ESI+): m/z=525.4.

Sources & evidence

ORD record
ord-31ccb2e26b1d4253893d53bec648f438
Source dataset
uspto-grants-2007_05
Patent number
US07211601B2

Reaction notes

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