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

HRID 449403Notes

Reaction equation

HRID 449403 reaction equation
[CH:1]1([NH2:10])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[C:11](Cl)(Cl)=[O:12].Cl.[CH3:16][N:17]1[CH2:22][CH2:21][N:20]([C:23]2[CH:28]=[C:27]([C:29]3[CH:38]=[C:37]4[C:32]([CH2:33][CH2:34][NH:35][CH2:36]4)=[CH:31][CH:30]=3)[N:26]=[C:25]([NH2:39])[N:24]=2)[CH2:19][CH2:18]1>>[NH2:39][C:25]1[N:26]=[C:27]([C:29]2[CH:38]=[C:37]3[C:32]([CH2:33][CH2:34][N:35]([C:11]([NH:10][CH:1]4[C:9]5[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=5)[CH2:3][CH2:2]4)=[O:12])[CH2:36]3)=[CH:31][CH:30]=2)[CH:28]=[C:23]([N:20]2[CH2:19][CH2:18][N:17]([CH3:16])[CH2:22][CH2:21]2)[N:24]=1

Participants

4

Reactant 3

HCID 6371PhosgeneHCID 123445(+-)-1-AminoindanHCID 675414894-(4-methylpiperazin-1-yl)-6-(1,2,3,4-tetrahydroisoquinolin-7-yl)pyrimidin-2-amine HCl salt

Product 1

HCID 497796477-[2-Amino-6-(4-methylpiperazin-1-yl)pyrimidin-4-yl]-N-(2,3-dihydro-1H-inden-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 2,3-dihydro-1H-inden-1-amine (Aldrich, Cat. #A59506), 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=484.2.

Workup

  1. customThis compound was prepared

Sources & evidence

ORD record
ord-520cbaf7c91141348355052017d54e7f
Source dataset
uspto-grants-2013_07
Patent number
US08481732B2

Reaction notes

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