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

HRID 449415Notes

Reaction equation

HRID 449415 reaction equation
[N:1]1([C:6]2[CH:12]=[CH:11][C:9]([NH2:10])=[CH:8][CH:7]=2)[CH:5]=[CH:4][CH:3]=[N:2]1.[C:13](Cl)(Cl)=[O:14].Cl.[CH3:18][N:19]1[CH2:24][CH2:23][N:22]([C:25]2[CH:30]=[C:29]([C:31]3[CH:40]=[C:39]4[C:34]([CH2:35][CH2:36][NH:37][CH2:38]4)=[CH:33][CH:32]=3)[N:28]=[C:27]([NH2:41])[N:26]=2)[CH2:21][CH2:20]1>>[NH2:41][C:27]1[N:28]=[C:29]([C:31]2[CH:40]=[C:39]3[C:34]([CH2:35][CH2:36][N:37]([C:13]([NH:10][C:9]4[CH:8]=[CH:7][C:6]([N:1]5[CH:5]=[CH:4][CH:3]=[N:2]5)=[CH:12][CH:11]=4)=[O:14])[CH2:38]3)=[CH:33][CH:32]=2)[CH:30]=[C:25]([N:22]2[CH2:21][CH2:20][N:19]([CH3:18])[CH2:24][CH2:23]2)[N:26]=1

Participants

4

Reactant 3

HCID 6371PhosgeneHCID 5942744-(1H-Pyrazol-1-yl)anilineHCID 675414894-(4-methylpiperazin-1-yl)-6-(1,2,3,4-tetrahydroisoquinolin-7-yl)pyrimidin-2-amine HCl salt

Product 1

HCID 594967137-[2-Amino-6-(4-methylpiperazin-1-yl)pyrimidin-4-yl]-N-[4-(1H-pyrazol-1-yl)phenyl]-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 4-(1H-pyrazol-1-yl)aniline (Maybridge, Cat. #CC 18414), 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=510.2.

Workup

  1. customThis compound was prepared

Sources & evidence

ORD record
ord-c57250812060474d8e1a601856552c3f
Source dataset
uspto-grants-2013_07
Patent number
US08481732B2

Reaction notes

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