Triethylamine → 4-[2-(4-Chlorobenzoyl)-1,2,3,4-tetrahydroisoquinolin-7-yl]-6-(4-methylpiperazin-1-yl)pyrimidin-2-amine

HRID 449312Notes

Reaction equation

HRID 449312 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.Cl.[CH3:12][N:13]1[CH2:18][CH2:17][N:16]([C:19]2[CH:24]=[C:23]([C:25]3[CH:34]=[C:33]4[C:28]([CH2:29][CH2:30][NH:31][CH2:32]4)=[CH:27][CH:26]=3)[N:22]=[C:21]([NH2:35])[N:20]=2)[CH2:15][CH2:14]1.C(N(CC)CC)C>O1CCCC1>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([N:31]2[CH2:30][CH2:29][C:28]3[C:33](=[CH:34][C:25]([C:23]4[CH:24]=[C:19]([N:16]5[CH2:15][CH2:14][N:13]([CH3:12])[CH2:18][CH2:17]5)[N:20]=[C:21]([NH2:35])[N:22]=4)=[CH:26][CH:27]=3)[CH2:32]2)=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 85014-Chlorobenzoyl chlorideHCID 675414894-(4-methylpiperazin-1-yl)-6-(1,2,3,4-tetrahydroisoquinolin-7-yl)pyrimidin-2-amine HCl salt

Product 1

HCID 594966724-[2-(4-Chlorobenzoyl)-1,2,3,4-tetrahydroisoquinolin-7-yl]-6-(4-methylpiperazin-1-yl)pyrimidin-2-amine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Chlorobenzoic acid chloride (4.4 μL, 0.034 mmol) was added to a mixture of 4-(4-methylpiperazin-1-yl)-6-(1,2,3,4-tetrahydroisoquinolin-7-yl)pyrimidin-2-amine HCl salt (10 mg, 0.02 mmol) and triethylamine (16 μL, 0.12 mmol) in tetrahydrofuran (0.3 mL). After 30 min, the mixture was purified by RP-LCMS (pH=10) to afford the desired products. Analytic LCMS (M+H)+: m/z=463.3/465.3

Workup

  1. customthe mixture was purified by RP-LCMS (pH=10)

Sources & evidence

ORD record
ord-14258937beb243ea9c4c8dc28126f142
Source dataset
uspto-grants-2013_07
Patent number
US08481732B2

Reaction notes

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