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

HRID 853912Notes

Reaction equation

HRID 853912 reaction equation
[N:1]1([CH2:7][C@@H:8]2[CH2:12][CH2:11][CH2:10][N:9]2[S:13]([C:16]2[CH:17]=[C:18]3[C:22](=[CH:23][CH:24]=2)[NH:21][C:20](=O)[C:19]3=[O:26])(=[O:15])=[O:14])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.Cl[CH2:28][C:29]1([C:34]#[N:35])[CH2:33][CH2:32][CH2:31][CH2:30]1>>[N:1]1([CH2:7][C@@H:8]2[CH2:12][CH2:11][CH2:10][N:9]2[S:13]([C:16]2[CH:24]=[CH:23][C:22]3[N:21]4[CH2:28][C:29]5([CH2:33][CH2:32][CH2:31][CH2:30]5)[CH2:34][N:35]=[C:20]4[C:19](=[O:26])[C:18]=3[CH:17]=2)(=[O:14])=[O:15])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 142045921-(Chloromethyl)cyclopentane-1-carbonitrileHCID 589325635-{[(2S)-2-(morpholin-4-ylmethyl)pyrrolidin-1-yl]sulfonyl}-1H-indole-2,3-dione

Product 1

HCID 115400978'-{[(2S)-2-(morpholin-4-ylmethyl)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 orange solid from 5-{[(2S)-2-(morpholin-4-ylmethyl)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 3-5 of Example 12. NMR (400 Mz, DMSO-d6): consistent. MS: (ES−) m/z 471 [M−H]. m.p.: 162.9-163.6° C.

Sources & evidence

ORD record
ord-3407a49fbe6d4bd288713b76e90b45b0
Source dataset
uspto-grants-2007_08
Patent number
US07256198B2

Reaction notes

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