Triethylamine → N-{2-[N-(5-chloro(2-pyridyl))carbamoyl]phenyl} (4-{[(1-methyl(2-imidazolin-2-yl))amino]methyl}phenyl)carboxamide

HRID 12166Notes

Reaction equation

HRID 12166 reaction equation
[NH2:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[C:18](=[O:27])[NH:19][C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][N:21]=2)=[O:10])=[CH:5][CH:4]=1.[CH3:28][N:29]1[CH2:33][CH2:32][N:31]=[C:30]1SC.CCN(CC)CC>N1C=CC=CC=1>[Cl:26][C:23]1[CH:24]=[CH:25][C:20]([NH:19][C:18]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[NH:11][C:9]([C:6]2[CH:5]=[CH:4][C:3]([CH2:2][NH:1][C:30]3[N:29]([CH3:28])[CH2:33][CH2:32][N:31]=3)=[CH:8][CH:7]=2)=[O:10])=[O:27])=[N:21][CH:22]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 103968741-methyl-2-methylsulfanyl-4,5-dihydro-1H-imidazoleHCID 18727608[4-(Aminomethyl)phenyl]-n-{2-[n-(5-chloro(2-pyridyl))carbamoyl]phenyl}carboxamide

Product 1

HCID 22596379N-{2-[N-(5-chloro(2-pyridyl))carbamoyl]phenyl} (4-{[(1-methyl(2-imidazolin-2-yl))amino]methyl}phenyl)carboxamideYield 65%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of [4-(aminomethyl)phenyl]-N-{2-[N-(5-chloro(2-pyridyl))carbamoyl]phenyl}carboxamide (74 mg, 0.195 mmol), 1-methyl-2-methylthio-2-imidazoline (25 mg, 0.195 mmol), NEt3 (2 mL) and pyridine (5 mL) was stirred at 80° C. overnight, concentrated and HPLC (C18 reversed phase) eluting with 0.1% TFA in H2O/CH3CN gave N-{2-[N-(5-chloro(2-pyridyl))carbamoyl]phenyl}(4-{[(1-methyl(2-imidazolin-2-yl))amino]methyl}phenyl)carboxamide (52 mg, 65%). MS found for C24H23ClN6O2 (M+H)+: 463.

Workup

  1. concentrationconcentrated
  2. washHPLC (C18 reversed phase) eluting with 0.1% TFA in H2O/CH3CN

Sources & evidence

ORD record
ord-30a4b1acec744fe7ac7ca91be30e3f4f
Source dataset
uspto-grants-2010_06
Patent number
US07727981B2

Reaction notes

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