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

HRID 853917Notes

Reaction equation

HRID 853917 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]12OCC[O:22]1)(=[O:11])=[O:10].Cl[CH2:27][C:28]1([C:35]#[N:36])[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]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[CH2:27][C:28]4([CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]4)[CH2:35][N:36]=[C:16]3[C:15](=[O:22])[C:14]=2[CH:13]=1)(=[O:10])=[O:11]

Participants

3

Reactant 2

HCID 142045931-(Chloromethyl)cycloheptane-1-carbonitrileHCID 58932534HCID 58932534, compound

Product 1

HCID 114960148'-{[(2S)-2-(methoxymethyl)pyrrolidin-1-yl]sulfonyl}spiro[cycloheptane-1,3'-pyrimido[1,2-a]indol]-10'(2'H)-one

Procedure

The title compound was prepared as a yellow foam from 5′-{[(2S)-2-(methoxymethyl)pyrrolidin-1-yl]sulfonyl}spiro[1,3-dioxolane-2,3′-indol]-2′(1′H)-one and 1-chloromethyl-cycloheptanecarbonitrile (Syn. Comm. 20(12) 1757, 1990) using a procedure similar to that of steps 3-5 of Example 12. The crude product was purified on Biotage KP silica gel eluting with CH2Cl2/EtOAc (9:1). NMR (400 Mz, DMSO-d6): consistent. Analytical HPLC (Chromolith Monolith 0.46×10 cm column, gradient of acetonitrile in water/trifluoroacetic acid): 93.2% (254 nm). MS: (API-ES+) m/z 446.2 [M+H]; (API-ES−) m/z 444.2 [M−H].

Workup

  1. customThe crude product was purified on Biotage KP silica gel eluting with CH2Cl2/EtOAc (9:1)

Sources & evidence

ORD record
ord-c03f7b4e21a14db395b01fd56177f908
Source dataset
uspto-grants-2007_08
Patent number
US07256198B2

Reaction notes

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