Ethanolamine → HCID 9880196, compound

HRID 1838214Notes

Reaction equation

HRID 1838214 reaction equation
CS[C:3]1[N:4]=[N:5][C:6]([C:21]#[N:22])=[C:7]([N:9]2[CH2:14][CH:13]=[C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH2:11][CH2:10]2)[N:8]=1.[CH2:23]([CH2:25][NH2:26])[OH:24]>O1CCOCC1>[OH:24][CH2:23][CH2:25][NH:26][C:3]1[N:4]=[N:5][C:6]([C:21]#[N:22])=[C:7]([N:9]2[CH2:14][CH:13]=[C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH2:11][CH2:10]2)[N:8]=1

Participants

4

Reactant 2

HCID 700EthanolamineHCID 18753282HCID 18753282, compound

Product 1

HCID 9880196HCID 9880196, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 68 mg (0.21 mmol) of 3-methylsulfanyl-5-(4-phenyl-3,6-dihydro-2H-pyridin-1-yl)-[1,2,4]triazine-6-carbonitrile and 14.5 mg (0.23 mmol) ethanolamine in 1 ml of dioxane was stirred at 120° C. overnight. For the working-up, the solution was evaporated under reduced pressure and the residue was chromatographed on silica gel with a 90:10:0.1 mixture of dichloromethane, methanol, and ammonium hydroxide as the eluent. There were obtained 35 mg (0.10 mmol, 50% of theory) of 3-(2-hydroxy-ethylamino)-5-(4-phenyl-3,6-dihydro-2H-pyridin-1-yl)-[1,2,4]triazine-6-carbonitrile as an amorphous, white solid; MS: 323 (M+H)+;

Workup

  1. customthe solution was evaporated under reduced pressure
  2. customthe residue was chromatographed on silica gel with a 90:10:0.1 mixture of dichloromethane, methanol, and ammonium hydroxide as the eluent

Sources & evidence

ORD record
ord-e694e8ff1b07493996552f4ba3bf98e1
Source dataset
uspto-grants-2004_01
Patent number
US06673795B2

Reaction notes

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