Phosgene → 7-[2-Amino-6-(4-methylpiperazin-1-yl)pyrimidin-4-yl]-N-(1,2,3,4-tetrahydronaphthalen-1-yl)-3,4-dihydroisoquinoline-2(1H)-carboxamide

HRID 449404Notes

Reaction equation

HRID 449404 reaction equation
[CH:1]1([NH2:11])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.[C:12](Cl)(Cl)=[O:13].Cl.[CH3:17][N:18]1[CH2:23][CH2:22][N:21]([C:24]2[CH:29]=[C:28]([C:30]3[CH:39]=[C:38]4[C:33]([CH2:34][CH2:35][NH:36][CH2:37]4)=[CH:32][CH:31]=3)[N:27]=[C:26]([NH2:40])[N:25]=2)[CH2:20][CH2:19]1>>[NH2:40][C:26]1[N:27]=[C:28]([C:30]2[CH:39]=[C:38]3[C:33]([CH2:34][CH2:35][N:36]([C:12]([NH:11][CH:1]4[C:10]5[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=5)[CH2:4][CH2:3][CH2:2]4)=[O:13])[CH2:37]3)=[CH:32][CH:31]=2)[CH:29]=[C:24]([N:21]2[CH2:20][CH2:19][N:18]([CH3:17])[CH2:23][CH2:22]2)[N:25]=1

Participants

4

Reactant 3

HCID 6371PhosgeneHCID 180661,2,3,4-Tetrahydro-1-naphthylamineHCID 675414894-(4-methylpiperazin-1-yl)-6-(1,2,3,4-tetrahydroisoquinolin-7-yl)pyrimidin-2-amine HCl salt

Product 1

HCID 497796487-[2-Amino-6-(4-methylpiperazin-1-yl)pyrimidin-4-yl]-N-(1,2,3,4-tetrahydronaphthalen-1-yl)-3,4-dihydroisoquinoline-2(1H)-carboxamide

Procedure

This compound was prepared by using procedures analogous to those described for the synthesis of Example 40 starting from 1,2,3,4-tetrahydronaphthalen-1-amine (Aldrich, Cat. #247820), phosgene and 4-(4-methylpiperazin-1-yl)-6-(1,2,3,4-tetrahydroisoquinolin-7-yl)pyrimidin-2-amine HCl salt. Analytic LCMS (M+H)+: m/z=498.3.

Workup

  1. customThis compound was prepared

Sources & evidence

ORD record
ord-4d775346e1f24a4881e18a0a5ddb4683
Source dataset
uspto-grants-2013_07
Patent number
US08481732B2

Reaction notes

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