1-(Chloromethyl)cyclopentane-1-carbonitrile → 8'-({(2S)-2-[(4-Methylpiperazin-1-yl)methyl]pyrrolidin-1-yl}sulfonyl)spiro[cyclopentane-1,3'-pyrimido[1,2-a]indol]-10'(2'H)-one

HRID 853916Notes

Reaction equation

HRID 853916 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][C@@H:9]2[CH2:13][CH2:12][CH2:11][N:10]2[S:14]([C:17]2[CH:18]=[C:19]3[C:23](=[CH:24][CH:25]=2)[NH:22][C:21](=O)[C:20]3=[O:27])(=[O:16])=[O:15])[CH2:4][CH2:3]1.Cl[CH2:29][C:30]1([C:35]#[N:36])[CH2:34][CH2:33][CH2:32][CH2:31]1>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([CH2:8][C@@H:9]2[CH2:13][CH2:12][CH2:11][N:10]2[S:14]([C:17]2[CH:25]=[CH:24][C:23]3[N:22]4[CH2:29][C:30]5([CH2:34][CH2:33][CH2:32][CH2:31]5)[CH2:35][N:36]=[C:21]4[C:20](=[O:27])[C:19]=3[CH:18]=2)(=[O:16])=[O:15])[CH2:6][CH2:7]1

Participants

3

Reactant 2

HCID 142045921-(Chloromethyl)cyclopentane-1-carbonitrileHCID 589325865-({(2S)-2-[(4-methylpiperazin-1-yl)methyl]pyrrolidin-1-yl}sulfonyl)-1H-indole-2,3-dione

Product 1

HCID 115331848'-({(2S)-2-[(4-Methylpiperazin-1-yl)methyl]pyrrolidin-1-yl}sulfonyl)spiro[cyclopentane-1,3'-pyrimido[1,2-a]indol]-10'(2'H)-one

Procedure

The title compound was prepared as a light brown foam from 5-({(2S)-2-[(4-methylpiperazin-1-yl)methyl]pyrrolidin-1-yl}sulfonyl)-1H-indole-2,3-dione and 1-(chloromethyl)cyclopentanecarbonitrile (Syn. Comm. 20(12) 1757, 1990), using a procedure similar to that of steps 2-5 of Example 12. NMR (400 Mz, DMSO-d6): consistent. MS: (ES+) m/z 486.2 [M+H].

Sources & evidence

ORD record
ord-def2a80811b3456fba1a2ef9516e67e9
Source dataset
uspto-grants-2007_08
Patent number
US07256198B2

Reaction notes

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