Triethylamine → n-{2-[(5-Chloro(2-pyridyl))carbamoyl]phenyl}{4-[(2-imidazolin-2-ylamino)methyl]phenyl}carboxamide

HRID 514730Notes

Reaction equation

HRID 514730 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.I.CS[C:31]1[NH:32][CH2:33][CH2:34][N:35]=1.C(N(CC)CC)C>CN(C=O)C>[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:31]3[NH:35][CH2:34][CH2:33][N:32]=3)=[CH:8][CH:7]=2)=[O:10])=[O:27])=[N:21][CH:22]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 122212281H-Imidazole, 4,5-dihydro-2-(methylthio)-, hydriodide (1:1)HCID 18727608[4-(Aminomethyl)phenyl]-n-{2-[n-(5-chloro(2-pyridyl))carbamoyl]phenyl}carboxamide

Product 1

HCID 18728105n-{2-[(5-Chloro(2-pyridyl))carbamoyl]phenyl}{4-[(2-imidazolin-2-ylamino)methyl]phenyl}carboxamideYield 15%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of [4-(aminomethyl)phenyl]-N-{2-[N-(5-chloro(2-pyridyl))carbamoyl]phenyl}carboxamide (80 mg, 0.21 mmol), 2-methylthio-2-imidazoline hydriodide (77 mg, 0.315 mmol, 1.5 equiv.) and triethyl amine (0.5 mL) in 1 mL DMF was stirred at room temperature overnight, concentrated to dryness and HPLC (C18 reversed phase) eluting with 0.1% TFA in H2O/CH3CN gave N-{2-[N-(5-chloro(2-pyridyl))carbamoyl]phenyl}{4-[(2-imidazolin-2-ylamino)methyl]phenyl}carboxamide (13.5 mg, 15%). MS found for C23H21ClN6O2 (M+H)+: 449

Workup

  1. concentrationconcentrated to dryness and HPLC (C18 reversed phase)
  2. washeluting with 0.1% TFA in H2O/CH3CN

Sources & evidence

ORD record
ord-31a07917fbd74e279425e687028ad237
Source dataset
uspto-grants-2015_08
Patent number
US09108922B2

Reaction notes

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