4-(((2-Aminoethyl)thio)methyl)-5-methylimidazole → 2-[2-(5-Methyl-4-imidazolylmethylthio)ethyl]amino-3-benzyloxypyridine

HRID 464381

Reaction equation

HRID 464381 reaction equation
[CH3:1][C:2]1[NH:6][CH:5]=[N:4][C:3]=1[CH2:7][S:8][CH2:9][CH2:10][NH2:11].Cl[C:13]1[C:18]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:17][CH:16]=[CH:15][N:14]=1>>[CH3:1][C:2]1[NH:6][CH:5]=[N:4][C:3]=1[CH2:7][S:8][CH2:9][CH2:10][NH:11][C:13]1[C:18]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:17][CH:16]=[CH:15][N:14]=1

Participants

3

Reactant 2

HCID 6655684-(((2-Aminoethyl)thio)methyl)-5-methylimidazoleHCID 8193743-(Benzyloxy)-2-chloropyridine

Product 1

HCID 155952532-[2-(5-Methyl-4-imidazolylmethylthio)ethyl]amino-3-benzyloxypyridineYield 9.8%

Procedure

2-(5-Methyl-4-imidazolylmethylthio)ethylamine (18.13 g; 0.105 moles) and 2-chloro-3-benzyloxypyridine (11.63 g; 0.053 moles) were mixed and heated to 120° for 9 days. The resulting reaction mixture was purified by chromatography using silica-gel, and chloroform as eluant. The red oil obtained, corresponding to 2-[2-(5-methyl-4-imidazolylmethylthio)ethyl]amino-3-benzyloxypyridine (1.85 g), was used in the next step without further purification.

Workup

  1. temperatureheated to 120° for 9 days
  2. customThe resulting reaction mixture
  3. customwas purified by chromatography

Sources & evidence

ORD record
ord-2ace9126dff2472ca258131656ddd46e
Source dataset
uspto-grants-1985_10
Patent number
US04547512

Linked notes

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