N-Methylethylenediamine → HCID 178438043, compound

HRID 1519829Notes

Reaction equation

HRID 1519829 reaction equation
[Cl:1][C:2]1[C:6]2[C:7]3[N:8]([C:11]([CH2:14][CH3:15])=[N:12][N:13]=3)C=[N:10][C:5]=2[S:4][CH:3]=1.CNCCN>CO.[Cl-].[NH4+]>[Cl:1][C:2]1[C:6]([C:7]2[NH:13][N:12]=[C:11]([CH2:14][CH3:15])[N:8]=2)=[C:5]([NH2:10])[S:4][CH:3]=1

Participants

5

Reactant 2

HCID 8014N-MethylethylenediamineHCID 687851919-Chloro-3-ethylthieno[3,2-e][1,2,4]triazolo[4,3-c]pyrimidine

Product 1

HCID 178438043HCID 178438043, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 25517Ammonium ChlorideSolvent

Procedure

9-Chloro-3-ethylthieno[3,2-e][1,2,4]triazolo[4,3-c]pyrimidine (20 mg, 83.8 umol) and N-methylethane-1,2-diamine (0.05 ml, 5.67 umol) in methanol (2 ml) was placed into a preheated oil bath at 60° C. After stirring for 15 min, the solution was diluted with saturated ammonium chloride and extracted with methylene chloride. The combined organic extracts were dried over magnesium sulfate, filtered, and concentrated under reduced pressure to afford 18 mg (94% yield) of 4-chloro-3-(3-ethyl-1H-1,2,4-triazol-5-yl)thiophen-2-amine as a brown solid. Method [8] Retention time 2.63 min by HPLC (M+ 229 and 231).

Workup

  1. extractionextracted with methylene chloride
  2. dry with materialThe combined organic extracts were dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b85cdb9a13ad435e850b385641caf734
Source dataset
uspto-grants-2015_07
Patent number
US09073891B2

Reaction notes

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