3-Amino-9-ethylcarbazole → (2S,4EZ)-4-benzylidene-N-(9-ethyl-9H-carbazol-3-yl)-1-[(2-oxo-6-pentyl-2H-pyran-3-yl)carbonyl]-2-pyrrolidinecarboxamide

HRID 1349190Notes

Reaction equation

HRID 1349190 reaction equation
[CH:1](=[C:8]1[CH2:12][N:11]([C:13]([O:15]C(C)(C)C)=O)[C@H:10]([C:20]([OH:22])=O)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:23]=[C:24]1[C:29](C(Cl)=O)=[CH:28][CH:27]=[C:26]([CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[O:25]1.[CH2:38]([N:40]1[C:52]2[CH:51]=[CH:50][C:49]([NH2:53])=[CH:48][C:47]=2[C:46]2[C:41]1=[CH:42][CH:43]=[CH:44][CH:45]=2)[CH3:39]>>[CH:1](=[C:8]1[CH2:12][N:11]([C:13]([C:29]2[C:24](=[O:23])[O:25][C:26]([CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])=[CH:27][CH:28]=2)=[O:15])[C@H:10]([C:20]([NH:53][C:49]2[CH:50]=[CH:51][C:52]3[N:40]([CH2:38][CH3:39])[C:41]4[C:46]([C:47]=3[CH:48]=2)=[CH:45][CH:44]=[CH:43][CH:42]=4)=[O:22])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 85883-Amino-9-ethylcarbazoleHCID 222235122-oxo-6-pentyl-2H-pyran-3-carbonyl chlorideHCID 69250545(2S,4EZ)-4benzylidene-1-(tert-butoxycarbonyl)-2-pyrrolidinecarboxylic acid

Product 1

HCID 69250432(2S,4EZ)-4-benzylidene-N-(9-ethyl-9H-carbazol-3-yl)-1-[(2-oxo-6-pentyl-2H-pyran-3-yl)carbonyl]-2-pyrrolidinecarboxamide

Procedure

Following the general method as outlined in Example 22, starting from (2S,4EZ)-4-benzylidene-1-(tert-butoxycarbonyl)-2-pyrrolidinecarboxylic acid, 2-oxo-6-pentyl-2H-pyran-3-carbonyl chloride, and 9-ethyl-9H-carbazol-3-amine the title compound was obtained in 47% purity by LC/MS. MS(ESI+): m/z=588.4.

Sources & evidence

ORD record
ord-159739e6686f449c8eedf48fc2e0069d
Source dataset
uspto-grants-2007_05
Patent number
US07211601B2

Reaction notes

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