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

HRID 449352Notes

Reaction equation

HRID 449352 reaction equation
[F:1][C:2]([F:10])([F:9])[C:3]1[N:4]=[C:5]([NH2:8])[S:6][CH:7]=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:8][C:5]4[S:6][CH:7]=[C:3]([C:2]([F:10])([F:9])[F:1])[N:4]=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 12014172-Thiazolamine, 4-(trifluoromethyl)-HCID 675414894-(4-methylpiperazin-1-yl)-6-(1,2,3,4-tetrahydroisoquinolin-7-yl)pyrimidin-2-amine HCl salt

Product 1

HCID 594965907-[2-Amino-6-(4-methylpiperazin-1-yl)pyrimidin-4-yl]-N-[4-(trifluoromethyl)-1,3-thiazol-2-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 4-(trifluoromethyl)-1,3-thiazol-2-amine (Oakwood, Cat. #009875), 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=519.2.

Workup

  1. customThis compound was prepared

Sources & evidence

ORD record
ord-750dcc79663c4c73a88e15a79ac0e16f
Source dataset
uspto-grants-2013_07
Patent number
US08481732B2

Reaction notes

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