3-Amino-9-ethylcarbazole → (2S,4EZ)-4-[(allyloxy)imino]-1-[4-(dimethylamino)butanoyl]-N-(9-ethyl-9H-carbazol-3-yl)-2-pyrrolidinecarboxamide

HRID 1349110Notes

Reaction equation

HRID 1349110 reaction equation
[CH2:1]([O:4][N:5]=[C:6]1[CH2:10][N:9]([C:11]([O:13]C(C)(C)C)=O)[C@H:8]([C:18]([OH:20])=O)[CH2:7]1)[CH:2]=[CH2:3].[CH3:21][N:22]([CH3:29])[CH2:23][CH2:24][CH2:25]C(Cl)=O.[CH2:30]([N:32]1[C:44]2[CH:43]=[CH:42][C:41]([NH2:45])=[CH:40][C:39]=2[C:38]2[C:33]1=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH3:31]>>[CH2:1]([O:4][N:5]=[C:6]1[CH2:10][N:9]([C:11](=[O:13])[CH2:25][CH2:24][CH2:23][N:22]([CH3:29])[CH3:21])[C@H:8]([C:18]([NH:45][C:41]2[CH:42]=[CH:43][C:44]3[N:32]([CH2:30][CH3:31])[C:33]4[C:38]([C:39]=3[CH:40]=2)=[CH:37][CH:36]=[CH:35][CH:34]=4)=[O:20])[CH2:7]1)[CH:2]=[CH2:3]

Participants

4

Reactant 3

HCID 85883-Amino-9-ethylcarbazoleHCID 150876904-(Dimethylamino)butanoyl chlorideHCID 58714562(2S,4EZ)-4-[(allyloxy)imino)-1-(tert-butoxycarbonyl)-2-pyrrolidinecarboxylic acid

Product 1

HCID 131725479(2S,4EZ)-4-[(allyloxy)imino]-1-[4-(dimethylamino)butanoyl]-N-(9-ethyl-9H-carbazol-3-yl)-2-pyrrolidinecarboxamide

Procedure

Following the general method as outlined in Example 22, starting from (2S,4EZ)-4-[(allyloxy)imino]-1-(tert-butoxycarbonyl)-2-pyrrolidinecarboxylic acid, 4-(dimethylamino)-butanoyl chloride and 9-ethyl-9H-carbazol-3-amine the title compound was obtained in 40% purity by LC/MS. MS(ESI+): m/z=490.4.

Sources & evidence

ORD record
ord-d6f0d34ed7d84c3d9d2890f0a8627dd7
Source dataset
uspto-grants-2007_05
Patent number
US07211601B2

Reaction notes

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