Diisopropylethylamine → HCID 178430548, compound

HRID 853009Notes

Reaction equation

HRID 853009 reaction equation
[NH2:1][CH2:2][C:3]1[CH:8]=[N:7][C:6]([CH3:9])=[CH:5][N:4]=1.[S:10]1[CH2:16][C:14](=[O:15])[NH:13][C:11]1=S.CCN(C(C)C)C(C)C>C(#N)C>[CH3:9][C:6]1[N:7]=[CH:8][C:3]([CH2:2][NH:1][C:11]2[S:10][CH2:16][C:14](=[O:15])[N:13]=2)=[N:4][CH:5]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 1201546RhodanineHCID 27564962-(Aminomethyl)-5-methylpyrazine

Product 1

HCID 178430548HCID 178430548, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-(aminomethyl)-5-methyl-pyrazine (3.69 g, 30 mmol) and Rhodanine (3.59 g, 27 mmol) in acetonitrile (100 mL) was added DIPEA (10.45 mL, 60 mmol) at room temperature. Then, this solution was cooled to 0° C. and mercuric chloride (8.15 g, 30 mmol) was added in two portions within 10 min. After addition, the suspension was allowed to warm to room temperature and stirred for 3 days. The resulting black solids were filtered through a plug of celite and washed with acetonitrile (1.0 L) and ethyl acetate (500 mL). The combined solvents were removed under the vacuum and the crude residue was dissolved in acetonitrile (25 mL) at hot condition. After cooling in the refrigerator overnight, the solids were collected by filtration and washed with acetonitrile. After drying in air, 1.5 g (25% yield) of 2-[(5-methyl-pyrazin-2-ylmethyl)-amino]-thiazol-4-one was isolated as a white solid: HRES(+) m/e calcd for C9H10N4OS (M+H)+223.0648, found 223.0648.

Workup

  1. additionAfter addition
  2. temperatureto warm to room temperature
  3. filtrationThe resulting black solids were filtered through a plug of celite
  4. washwashed with acetonitrile (1.0 L) and ethyl acetate (500 mL)
  5. customThe combined solvents were removed under the vacuum
  6. dissolutionthe crude residue was dissolved in acetonitrile (25 mL) at hot condition
  7. temperatureAfter cooling in the refrigerator overnight
  8. filtrationthe solids were collected by filtration
  9. washwashed with acetonitrile
  10. customAfter drying in air

Sources & evidence

ORD record
ord-d31abe0e3e42457398f5c6de297a9ee5
Source dataset
uspto-grants-2007_08
Patent number
US07253285B2

Reaction notes

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