Ethanolamine → 5-{2-[2-Amino-6-(4-methylpiperazin-1-yl)pyrimidin-4-yl]-3-methyl-1,2,3,4-tetrahydroisoquinolin-7-yl}-N-(2-hydroxyethyl)pyridine-2-carboxamide

HRID 2090359Notes

Reaction equation

HRID 2090359 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([N:8]2[CH:17]([CH3:18])[CH2:16][C:15]3[C:10](=[CH:11][C:12]([C:19]4[CH:20]=[CH:21][C:22]([C:25]([OH:27])=O)=[N:23][CH:24]=4)=[CH:13][CH:14]=3)[CH2:9]2)[CH:5]=[C:4]([N:28]2[CH2:33][CH2:32][N:31]([CH3:34])[CH2:30][CH2:29]2)[N:3]=1.[CH2:35]([CH2:37][NH2:38])[OH:36]>>[NH2:1][C:2]1[N:7]=[C:6]([N:8]2[CH:17]([CH3:18])[CH2:16][C:15]3[C:10](=[CH:11][C:12]([C:19]4[CH:20]=[CH:21][C:22]([C:25]([NH:38][CH2:37][CH2:35][OH:36])=[O:27])=[N:23][CH:24]=4)=[CH:13][CH:14]=3)[CH2:9]2)[CH:5]=[C:4]([N:28]2[CH2:29][CH2:30][N:31]([CH3:34])[CH2:32][CH2:33]2)[N:3]=1

Participants

3

Reactant 2

HCID 700EthanolamineHCID 594023605-{2-[2-Amino-6-(4-methylpiperazin-1-yl)pyrimidin-4-yl]-3-methyl-1,2,3,4-tetrahydroisoquinolin-7-yl}pyridine-2-carboxylic acid

Product 1

HCID 467017245-{2-[2-Amino-6-(4-methylpiperazin-1-yl)pyrimidin-4-yl]-3-methyl-1,2,3,4-tetrahydroisoquinolin-7-yl}-N-(2-hydroxyethyl)pyridine-2-carboxamide

Procedure

This compound was prepared by using procedures analogous to those described for the synthesis of Example 50B starting from 5-{2-[2-amino-6-(4-methylpiperazin-1-yl)pyrimidin-4-yl]-3-methyl-1,2,3,4-tetrahydroisoquinolin-7-yl}pyridine-2-carboxylic acid (Example 50B, Step 1) and ethanolamine (Aldrich, Cat. No. 411000). LCMS (M+H)+: m/z=503.2.

Workup

  1. customThis compound was prepared
  2. customthose described for the synthesis of Example 50B

Sources & evidence

ORD record
ord-eab3809897714bb2985844342202da9d
Source dataset
uspto-grants-2013_05
Patent number
US08436008B2

Reaction notes

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