Diisopropylethylamine → 5-Chloro-6-ethyl-3-{[3-(methylsulfonyl)phenyl]amino}pyrazine-2-carboxamide

HRID 869239ノート

反応式

HRID 869239 の反応式
Cl[C:2]1[C:3]([C:11]([NH2:13])=[O:12])=[N:4][C:5]([CH2:9][CH3:10])=[C:6]([Cl:8])[N:7]=1.[CH3:14][S:15]([C:18]1[CH:19]=[C:20]([CH:22]=[CH:23][CH:24]=1)[NH2:21])(=[O:17])=[O:16].C(N(CC)C(C)C)(C)C>O1CCOCC1>[Cl:8][C:6]1[N:7]=[C:2]([NH:21][C:20]2[CH:22]=[CH:23][CH:24]=[C:18]([S:15]([CH3:14])(=[O:17])=[O:16])[CH:19]=2)[C:3]([C:11]([NH2:13])=[O:12])=[N:4][C:5]=1[CH2:9][CH3:10]

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 4280293-(Methylsulphonyl)anilineHCID 848199603,5-Dichloro-6-ethylpyrazine-2-carboxamide

生成物 1

HCID 866620465-Chloro-6-ethyl-3-{[3-(methylsulfonyl)phenyl]amino}pyrazine-2-carboxamide収率 42.6%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

反応条件

温度
170 °C

実験手順

A mixture of 3,5-dichloro-6-ethylpyrazine-2-carboxamide (600 mg), 3-(methylsulfonyl)aniline (467 mg), N,N-diisopropylethylamine (0.48 mL) and dioxane (18 mL) was stirred in a sealed tube at 170° C. for 17 hours. After cooling, the mixture was partitioned using ethyl acetate and water, and the organic layer was washed with saturated aqueous sodium chloride and then dried over anhydrous magnesium sulfate. After the solvent was distilled off, the residue was washed with chloroform, and the solid was collected by filtration and dried to give 5-chloro-6-ethyl-3-{[3-(methylsulfonyl)phenyl]amino}pyrazine-2-carboxamide (412 mg) as a yellow solid.

後処理

  1. temperatureAfter cooling
  2. customthe mixture was partitioned
  3. washthe organic layer was washed with saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationAfter the solvent was distilled off
  6. washthe residue was washed with chloroform
  7. filtrationthe solid was collected by filtration
  8. customdried

出典と根拠

ORDレコード
ord-27e720ee5f934e30907ce03c2b10d89a
出典データセット
uspto-grants-2015_03
特許番号
US08969336B2

反応ノート

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