HCID 18180220, compound → 2-Isopropylcarbonylamino-6-amino-3-(2,3,5-trichlorophenyl)pyrazine

HRID 1358979Notes

Reaction equation

HRID 1358979 reaction equation
[CH:1]([C:4]([NH:6][C:7]1[C:12]([C:13]2[CH:18]=[C:17]([Cl:19])[CH:16]=[C:15]([Cl:20])[C:14]=2[Cl:21])=[N:11][CH:10]=[C:9]([NH:22]C(=O)C)[N:8]=1)=[O:5])([CH3:3])[CH3:2]>C(O)C>[CH:1]([C:4]([NH:6][C:7]1[C:12]([C:13]2[CH:18]=[C:17]([Cl:19])[CH:16]=[C:15]([Cl:20])[C:14]=2[Cl:21])=[N:11][CH:10]=[C:9]([NH2:22])[N:8]=1)=[O:5])([CH3:3])[CH3:2]

Participants

3

Reactant 1

HCID 18180220HCID 18180220, compound

Product 1

HCID 181802152-Isopropylcarbonylamino-6-amino-3-(2,3,5-trichlorophenyl)pyrazine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
55 °C

Procedure

Stannous chloride (0.182 g, 0.0096 mole) was added to the suspension of 2-isopropylcarbonylamino-6-acetamido-3-(2,3,5-trichlorophenyl)pyrazine (0.13 g, 3.24×10−4 mole), in absolute ethanol (6.50 ml) and the resulting mixture stirred at 50-60° C. for 1 hr 20 min. The reaction mixture was cooled and evaporated in vacuo. The residue was extracted with ethylacetate (3×20 ml), washed with water (2×20 ml), dried over anhydrous magnesium sulphate, filtered and the filtrate evaporated in vacuo. The residue was purified by ‘flash chromatography’ using chloroform:methanol, 99:1 as the eluent. Yield 0.046 g (40%), M.p. 105-108° C.

Workup

  1. temperatureThe reaction mixture was cooled
  2. customevaporated in vacuo
  3. extractionThe residue was extracted with ethylacetate (3×20 ml)
  4. washwashed with water (2×20 ml)
  5. dry with materialdried over anhydrous magnesium sulphate
  6. filtrationfiltered
  7. customthe filtrate evaporated in vacuo
  8. customThe residue was purified by ‘flash chromatography’

Sources & evidence

ORD record
ord-35e81cf6f751401296e0c2fbbab1daa2
Source dataset
uspto-grants-2003_07
Patent number
US06599905B2

Reaction notes

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