Diisopropylethylamine → 8-Chloro-[1,2,4]triazolo[1,5-a]pyrazin-2-yl-(6-methoxy-pyridin-3-yl)-amine

HRID 570601Notes

Reaction equation

HRID 570601 reaction equation
C1([C:9]([O-:11])=O)C=C(C)C=C(C)C=1.[NH2:12][N+:13]1[CH:18]=[CH:17][N:16]=[CH:15][C:14]=1[NH2:19].[CH:20]([N:23]([CH:26](C)C)CC)(C)C.CCN=C=N[CH2:34][CH2:35][CH2:36][N:37]([CH3:39])C.[ClH:40]>ClCCl>[Cl:40][C:15]1[C:14]2[N:13]([N:12]=[C:20]([NH:23][C:26]3[CH:39]=[N:37][C:36]([O:11][CH3:9])=[CH:35][CH:34]=3)[N:19]=2)[CH:18]=[CH:17][N:16]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 1317328011,2-Diamino-pyrazinium mesitylenate

Product 1

HCID 870591248-Chloro-[1,2,4]triazolo[1,5-a]pyrazin-2-yl-(6-methoxy-pyridin-3-yl)-amineYield 80.32%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-methoxypyridyl-5-isothiocyanate (3 g, 18.07 mmol) in dry dichloromethane (200 ml), 1,2-diamino-pyrazinium mesitylenate (7.77 g, 22.5 mmol), diisopropylethylamine (11.67 g, 90.35 mmol) and EDCl (3.44 g, 36.14 mmol) are added and stirred for 6 hours. The reaction mixture is concentrated and the residue is taken in water (100 ml), triturated and filtered, washed with water (50 ml×2) and 50% diethylether in hexane to get the titled product as light brown solid (4 g, 80.32%); TLC: chloroform/methanol (9.5/0.5) Rf-0.3;

Workup

  1. concentrationThe reaction mixture is concentrated
  2. customtriturated
  3. filtrationfiltered
  4. washwashed with water (50 ml×2) and 50% diethylether in hexane

Sources & evidence

ORD record
ord-512fc754bd1b4cef8e912abeb4965f78
Source dataset
uspto-grants-2015_05
Patent number
US09023851B2

Reaction notes

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