Ethylenediamine → HCID 72714946、化合物

HRID 77359ノート

反応式

HRID 77359 の反応式
[O:1]=[C:2]1[NH:7][C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=2)=[CH:5][N:4]2[C:18]([C:21]#[N:22])=[CH:19][CH:20]=[C:3]12.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=S.[CH2:37](N)[CH2:38][NH2:39]>>[NH:22]1[CH2:37][CH2:38][N:39]=[C:21]1[C:18]1[N:4]2[CH:5]=[C:6]([C:8]3[CH:13]=[CH:12][C:11]([C:14]([F:15])([F:17])[F:16])=[CH:10][CH:9]=3)[NH:7][C:2](=[O:1])[C:3]2=[CH:20][CH:19]=1

参加物

4

反応物 3

HCID 3301EthylenediamineHCID 14817Phosphorus sulfide (P2S5)HCID 727149431-Oxo-3-(4-trifluoromethyl-phenyl)-1,2-dihydro-pyrrolo[1,2-a]pyrazine-6-carbonitrile

生成物 1

HCID 72714946HCID 72714946、化合物収率 81.8%

反応条件

温度
120 °C

実験手順

A mixture of 1-oxo-3-(4-trifluoromethyl-phenyl)-1,2-dihydro-pyrrolo[1,2-a]pyrazine-6-carbonitrile (Example 2) (0.03 g, 98.9 μmol), phosphorus pentasulfide (8 mg, 36.0 μmol) and ethane-1,2-diamine (0.5 mL, 7.48 mmol) in a sealed vial was heated at 120° C. for 2 h. At this time, the green/yellow reaction mixture was allowed to cool to room temperature and was then poured onto ice water. The resulting solid was collected by filtration, washed with water and dried in vacuo to afford 6-(4,5-dihydro-1H-imidazol-2-yl)-3-(4-trifluoromethyl-phenyl)-2H-pyrrolo[1,2-a]pyrazin-1-one (28 mg, 81%) as light yellow solid. 1H NMR (methanol-d4) δ ppm 7.86-7.91 (m, 3H), 7.77-7.84 (m, 3H), 7.44 (d, J=0.8 Hz, 1H), 3.81 (s, 4H). LC-MS calcd. for C17H14F3N4O [(M+H)+] 347, obsd. 347.0.

後処理

  1. temperatureto cool to room temperature
  2. additionwas then poured onto ice water
  3. filtrationThe resulting solid was collected by filtration
  4. washwashed with water
  5. customdried in vacuo

出典と根拠

ORDレコード
ord-7f6780835ef6485ca92a327edb2542a4
出典データセット
uspto-grants-2014_09
特許番号
US08841299B2

反応ノート

読み込み中…