Ethylenediamine → HCID 72714946, 화합물

HRID 77359노트

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HRID 77359 반응식
[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

참가 물질

4

반응물 3

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

생성물 1

HCID 72714946HCID 72714946, 화합물수율 81.8%

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온도
120 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-7f6780835ef6485ca92a327edb2542a4
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841299B2

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