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

HRID 449464Notes

Reaction equation

HRID 449464 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]([NH2:9])[CH3:8])[CH:2]=1.[C:10](Cl)(Cl)=[O:11].Cl.[CH3:15][N:16]1[CH2:21][CH2:20][N:19]([C:22]2[CH:27]=[C:26]([C:28]3[CH:37]=[C:36]4[C:31]([CH2:32][CH2:33][NH:34][CH2:35]4)=[CH:30][CH:29]=3)[N:25]=[C:24]([NH2:38])[N:23]=2)[CH2:18][CH2:17]1>>[NH2:38][C:24]1[N:25]=[C:26]([C:28]2[CH:37]=[C:36]3[C:31]([CH2:32][CH2:33][N:34]([C:10]([NH:9][CH:7]([C:3]4[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=4)[CH3:8])=[O:11])[CH2:35]3)=[CH:30][CH:29]=2)[CH:27]=[C:22]([N:19]2[CH2:18][CH2:17][N:16]([CH3:15])[CH2:21][CH2:20]2)[N:23]=1

Participants

4

Reactant 3

HCID 6371PhosgeneHCID 27716881-(Pyridin-3-yl)ethan-1-amineHCID 675414894-(4-methylpiperazin-1-yl)-6-(1,2,3,4-tetrahydroisoquinolin-7-yl)pyrimidin-2-amine HCl salt

Product 1

HCID 594966667-[2-Amino-6-(4-methylpiperazin-1-yl)pyrimidin-4-yl]-N-(1-pyridin-3-ylethyl)-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-pyridin-3-ylethanamine (Enamine, Cat. #EN300-12752), 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=473.1.

Workup

  1. customThis compound was prepared

Sources & evidence

ORD record
ord-ac0b04f0e2f441c182ace1961aeb2e0c
Source dataset
uspto-grants-2013_07
Patent number
US08481732B2

Reaction notes

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