Diisopropylethylamine → 4-{2-[2-amino-6-(4-methylpiperazin-1-yl)pyrimidin-4-yl]-3-methyl-1,2,3,4-tetrahydroisoquinolin-7-yl}-N-cyclopentyl-3,6-dihydropyridine-1(2H)-carboxamide

HRID 2090482Notes

Reaction equation

HRID 2090482 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[C:12]([N:14]3[CH:23]([CH3:24])[CH2:22][C:21]4[C:16](=[CH:17][C:18]([C:25]5[CH2:26][CH2:27][NH:28][CH2:29][CH:30]=5)=[CH:19][CH:20]=4)[CH2:15]3)[N:11]=[C:10]([NH2:31])[N:9]=2)[CH2:4][CH2:3]1.C(N(CC)C(C)C)(C)C.[N:41]([CH:44]1[CH2:48][CH2:47][CH2:46][CH2:45]1)=[C:42]=[O:43]>CN(C)C=O.CO>[NH2:31][C:10]1[N:11]=[C:12]([N:14]2[CH:23]([CH3:24])[CH2:22][C:21]3[C:16](=[CH:17][C:18]([C:25]4[CH2:26][CH2:27][N:28]([C:42]([NH:41][CH:44]5[CH2:48][CH2:47][CH2:46][CH2:45]5)=[O:43])[CH2:29][CH:30]=4)=[CH:19][CH:20]=3)[CH2:15]2)[CH:13]=[C:8]([N:5]2[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]2)[N:9]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 643500Cyclopentyl IsocyanateHCID 59402262HCID 59402262, compound

Product 1

HCID 594022904-{2-[2-amino-6-(4-methylpiperazin-1-yl)pyrimidin-4-yl]-3-methyl-1,2,3,4-tetrahydroisoquinolin-7-yl}-N-cyclopentyl-3,6-dihydropyridine-1(2H)-carboxamide

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

4-(4-Methylpiperazin-1-yl)-6-[3-methyl-7-(1,2,3,6-tetrahydropyridin-4-yl)-3,4-dihydroisoquinolin-2(1H)-yl]pyrimidin-2-amine (21.0 mg) HCl salt in N,N-dimethylformamide (1.0 mL) was treated with N,N-diisopropylethylamine (0.070 mL, 0.40 mmol). To the solution was added isocyanatocyclopentane (11.1 mg, 0.100 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=531.2.

Workup

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

Sources & evidence

ORD record
ord-b0c739b0fd374c2cb65ddae0b0f873fc
Source dataset
uspto-grants-2013_05
Patent number
US08436008B2

Reaction notes

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