Phosgene → 7-[2-amino-6-(4-methylpiperazin-1-yl)pyrimidin-4-yl]-N-{4-[(dimethylamino)carbonyl]cyclohexyl}-3,4-dihydroisoquinoline-2(1H)-carboxamide

HRID 449358Notes

Reaction equation

HRID 449358 reaction equation
Cl.[NH2:2][CH:3]1[CH2:8][CH2:7][CH:6]([C:9]([N:11]([CH3:13])[CH3:12])=[O:10])[CH2:5][CH2:4]1.[C:14](Cl)(Cl)=[O:15].Cl.[CH3:19][N:20]1[CH2:25][CH2:24][N:23]([C:26]2[CH:31]=[C:30]([C:32]3[CH:41]=[C:40]4[C:35]([CH2:36][CH2:37][NH:38][CH2:39]4)=[CH:34][CH:33]=3)[N:29]=[C:28]([NH2:42])[N:27]=2)[CH2:22][CH2:21]1>>[NH2:42][C:28]1[N:29]=[C:30]([C:32]2[CH:41]=[C:40]3[C:35]([CH2:36][CH2:37][N:38]([C:14]([NH:2][CH:3]4[CH2:4][CH2:5][CH:6]([C:9]([N:11]([CH3:13])[CH3:12])=[O:10])[CH2:7][CH2:8]4)=[O:15])[CH2:39]3)=[CH:34][CH:33]=2)[CH:31]=[C:26]([N:23]2[CH2:22][CH2:21][N:20]([CH3:19])[CH2:25][CH2:24]2)[N:27]=1

Participants

4

Reactant 3

HCID 6371PhosgeneHCID 675414894-(4-methylpiperazin-1-yl)-6-(1,2,3,4-tetrahydroisoquinolin-7-yl)pyrimidin-2-amine HCl saltHCID 675415424-amino-N,N-dimethylcyclohexane-1-carboxamide hydrochloride

Product 1

HCID 594967027-[2-amino-6-(4-methylpiperazin-1-yl)pyrimidin-4-yl]-N-{4-[(dimethylamino)carbonyl]cyclohexyl}-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-amino-N,N-dimethylcyclohexanecarboxamide hydrochloride, 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=521.3.

Workup

  1. customThis compound was prepared

Sources & evidence

ORD record
ord-57738dc734534dc7907a8e22c20109b1
Source dataset
uspto-grants-2013_07
Patent number
US08481732B2

Reaction notes

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