1-(Chloromethyl)cyclopentane-1-carbonitrile → Pyrimidoindolone, 25c

HRID 853906Notes

Reaction equation

HRID 853906 reaction equation
[CH3:1][O:2][CH2:3][C@@H:4]1[CH2:8][CH2:7][CH2:6][N:5]1[S:9]([C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[NH:17][C:16](=O)[C:15]12OCCC[O:22]1)(=[O:11])=[O:10].Cl[CH2:28][C:29]1([C:34]#[N:35])[CH2:33][CH2:32][CH2:31][CH2:30]1>>[CH3:1][O:2][CH2:3][C@@H:4]1[CH2:8][CH2:7][CH2:6][N:5]1[S:9]([C:12]1[CH:20]=[CH:19][C:18]2[N:17]3[CH2:28][C:29]4([CH2:33][CH2:32][CH2:31][CH2:30]4)[CH2:34][N:35]=[C:16]3[C:15](=[O:22])[C:14]=2[CH:13]=1)(=[O:11])=[O:10]

Participants

3

Reactant 2

HCID 142045921-(Chloromethyl)cyclopentane-1-carbonitrileHCID 589325505'-{[(2S)-2-(methoxymethyl)pyrrolidin-1-yl]sulfonyl}spiro[1,3-dioxane-2,3'-indol]-2'(1'H)-one

Product 1

HCID 11567908Pyrimidoindolone, 25c

Procedure

The title compound was prepared as a yellow solid from 5′-{[(2S)-2-(methoxymethyl)pyrrolidin-1-yl]sulfonyl}spiro[1,3-dioxane-2,3′-indol]-2′(1′H)-one 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 416[M−H]. m.p.: 171.2-171.9° C.

Sources & evidence

ORD record
ord-4a4c49e21279453bad9ad9d447049438
Source dataset
uspto-grants-2007_08
Patent number
US07256198B2

Reaction notes

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