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

HRID 1349058Notes

Reaction equation

HRID 1349058 reaction equation
C(O[C:6]([N:8]1[CH2:15][C:14](=[CH2:16])[CH2:13][C@H:9]1[C:10]([OH:12])=O)=[O:7])(C)(C)C.[CH3:17][N:18]([CH3:25])[CH2:19][CH2:20][CH2:21]C(Cl)=O.[CH2:26]([N:28]1[C:40]2[CH:39]=[CH:38][C:37]([NH2:41])=[CH:36][C:35]=2[C:34]2[C:29]1=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH3:27]>>[CH3:17][N:18]([CH3:25])[CH2:19][CH2:20][CH2:21][C:6]([N:8]1[CH2:15][C:14](=[CH2:16])[CH2:13][C@H:9]1[C:10]([NH:41][C:37]1[CH:38]=[CH:39][C:40]2[N:28]([CH2:26][CH3:27])[C:29]3[C:34]([C:35]=2[CH:36]=1)=[CH:33][CH:32]=[CH:31][CH:30]=3)=[O:12])=[O:7]

Participants

4

Reactant 3

HCID 85883-Amino-9-ethylcarbazoleHCID 150876904-(Dimethylamino)butanoyl chlorideHCID 21727417(2S)-1-((tert-butoxy)carbonyl)-4-methylidenepyrrolidine-2-carboxylic acid

Product 1

HCID 69249213(2S)-1-[4-(dimethylamino)butanoyl]-N-(9-ethyl-9H-carbazol-3-yl)-4-methylene-2-pyrrolidinecarboxamide

Procedure

Following the general method as outlined in Example 22, starting from 1-(tert-butoxycarbonyl)-4-methyleneproline, 4-(dimethylamino)butanoyl chloride, and 9-ethyl-9H-carbazol-3-amine the title compound was obtained in 51% purity by LC/MS. MS(ESI+): m/z=433.6.

Sources & evidence

ORD record
ord-658d88c6dab04d5cac069acf6fd58a71
Source dataset
uspto-grants-2007_05
Patent number
US07211601B2

Reaction notes

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