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

HRID 853909Notes

Reaction equation

HRID 853909 reaction equation
[O:1]([CH2:8][C@@H:9]1[CH2:13][CH2:12][CH2:11][N:10]1[S:14]([C:17]1[CH:18]=[C:19]2[C:23](=[CH:24][CH:25]=1)[NH:22][C:21](=O)[C:20]12[O:31]CCCO1)(=[O:16])=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[CH2:33][C:34]1([C:39]#[N:40])[CH2:38][CH2:37][CH2:36][CH2:35]1>>[O:1]([CH2:8][C@@H:9]1[CH2:13][CH2:12][CH2:11][N:10]1[S:14]([C:17]1[CH:25]=[CH:24][C:23]2[N:22]3[CH2:33][C:34]4([CH2:38][CH2:37][CH2:36][CH2:35]4)[CH2:39][N:40]=[C:21]3[C:20](=[O:31])[C:19]=2[CH:18]=1)(=[O:16])=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 142045921-(Chloromethyl)cyclopentane-1-carbonitrileHCID 252690145'-{[(2S)-2-(phenoxymethyl)pyrrolidin-1-yl]sulfonyl}spiro[1,3-dioxane-2,3'-indol]-2'(1'H)-one

Product 1

HCID 11719933Pyrimidoindolone, 25d

Procedure

The title compound was prepared as a yellow solid from 5′-{[(2S)-2-(phenoxymethyl)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 478 [M−H]. m.p.: 142.9.8-144.5° C.

Workup

  1. custom9.8-144.5° C.

Sources & evidence

ORD record
ord-17c659a78886449f9dd58e840b6dce4e
Source dataset
uspto-grants-2007_08
Patent number
US07256198B2

Reaction notes

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