Diisopropylethylamine → 4-[7-[1-(cyclopentylacetyl)piperidin-4-yl]-3-methyl-3,4-dihydroisoquinolin-2(1H)-yl]-6-(4-methylpiperazin-1-yl)pyrimidin-2-amine

HRID 2090485Notes

Reaction equation

HRID 2090485 reaction equation
Cl.[CH3:2][N:3]1[CH2:8][CH2:7][N:6]([C:9]2[CH:14]=[C:13]([N:15]3[CH:24]([CH3:25])[CH2:23][C:22]4[C:17](=[CH:18][C:19]([CH:26]5[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]5)=[CH:20][CH:21]=4)[CH2:16]3)[N:12]=[C:11]([NH2:32])[N:10]=2)[CH2:5][CH2:4]1.C(N(CC)C(C)C)(C)C.[CH:42]1([CH2:47][C:48](Cl)=[O:49])[CH2:46][CH2:45][CH2:44][CH2:43]1>C(#N)C.CO>[CH:42]1([CH2:47][C:48]([N:29]2[CH2:28][CH2:27][CH:26]([C:19]3[CH:18]=[C:17]4[C:22]([CH2:23][CH:24]([CH3:25])[N:15]([C:13]5[CH:14]=[C:9]([N:6]6[CH2:7][CH2:8][N:3]([CH3:2])[CH2:4][CH2:5]6)[N:10]=[C:11]([NH2:32])[N:12]=5)[CH2:16]4)=[CH:21][CH:20]=3)[CH2:31][CH2:30]2)=[O:49])[CH2:46][CH2:45][CH2:44][CH2:43]1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 3485182Cyclopentylacetyl chlorideHCID 684710864-(4-Methylpiperazin-1-yl)-6-(3-methyl-7-piperidin-4-yl-3,4-dihydroisoquinolin-2(1H)-yl)pyrimidin-2-amine HCl salt

Product 1

HCID 594023824-[7-[1-(cyclopentylacetyl)piperidin-4-yl]-3-methyl-3,4-dihydroisoquinolin-2(1H)-yl]-6-(4-methylpiperazin-1-yl)pyrimidin-2-amine

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 HCl salt (21.1 mg) in acetonitrile (0.50 mL) was treated with N,N-diisopropylethylamine (0.070 mL, 0.40 mmol). To the solution was added cyclopentylacetyl chloride (10.0 mg). 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=532.3.

Workup

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

Sources & evidence

ORD record
ord-f2936b95c8394476a1b3e95f4d0d3dce
Source dataset
uspto-grants-2013_05
Patent number
US08436008B2

Reaction notes

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