Dimethylcarbamoyl Chloride → 4-{2-[2-Amino-6-(4-methylpiperazin-1-yl)pyrimidin-4-yl]-3-methyl-1,2,3,4-tetrahydroisoquinolin-7-yl}-N,N-dimethylpiperidine-1-carboxamide

HRID 2090498Notes

Reaction equation

HRID 2090498 reaction equation
Cl.Cl.Cl.Cl.[CH3:5][N:6]1[CH2:11][CH2:10][N:9]([C:12]2[CH:17]=[C:16]([N:18]3[CH:27]([CH3:28])[CH2:26][C:25]4[C:20](=[CH:21][C:22]([CH:29]5[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]5)=[CH:23][CH:24]=4)[CH2:19]3)[N:15]=[C:14]([NH2:35])[N:13]=2)[CH2:8][CH2:7]1.C(N(CC)C(C)C)(C)C.[CH3:45][N:46]([CH3:50])[C:47](Cl)=[O:48]>C(#N)C.CO>[NH2:35][C:14]1[N:15]=[C:16]([N:18]2[CH:27]([CH3:28])[CH2:26][C:25]3[C:20](=[CH:21][C:22]([CH:29]4[CH2:30][CH2:31][N:32]([C:47]([N:46]([CH3:50])[CH3:45])=[O:48])[CH2:33][CH2:34]4)=[CH:23][CH:24]=3)[CH2:19]2)[CH:17]=[C:12]([N:9]2[CH2:10][CH2:11][N:6]([CH3:5])[CH2:7][CH2:8]2)[N:13]=1

Participants

6

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 81531DiisopropylethylamineHCID 674348394-(4-Methylpiperazin-1-yl)-6-(3-methyl-7-piperidin-4-yl-3,4-dihydroisoquinolin-2(1H)-yl)pyrimidin-2-amine tetrahydrochloride

Product 1

HCID 594022494-{2-[2-Amino-6-(4-methylpiperazin-1-yl)pyrimidin-4-yl]-3-methyl-1,2,3,4-tetrahydroisoquinolin-7-yl}-N,N-dimethylpiperidine-1-carboxamide

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Procedure

4-(4-Methylpiperazin-1-yl)-6-(3-methyl-7-piperidin-4-yl-3,4-dihydroisoquinolin-2(1H)-yl)pyrimidin-2-amine tetrahydrochloride (17 mg) HCl salt in acetonitrile (0.50 mL) was treated with N,N-diisopropylethylamine (42 uL, 0.24 mmol). To the solution was added N,N-Dimethylcarbamoyl chloride (3.59 uL, 0.0390 mmol). The mixture was stirred at r.t. for 2 h. The mixture was diluted with methanol, and purified by RP-HPLC (pH=10) to afford the desired product. LCMS (M+H)+: m/z=493.4.

Workup

  1. custompurified by RP-HPLC (pH=10)

Sources & evidence

ORD record
ord-e822aa9f7af541bd9093a83ea6b0c690
Source dataset
uspto-grants-2013_05
Patent number
US08436008B2

Reaction notes

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