Ethylenediamine → HCID 72714946, compound

HRID 77359Notes

Reaction equation

HRID 77359 reaction equation
[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

Participants

4

Reactant 3

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

Product 1

HCID 72714946HCID 72714946, compoundYield 81.8%

Conditions

Temperature
120 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-7f6780835ef6485ca92a327edb2542a4
Source dataset
uspto-grants-2014_09
Patent number
US08841299B2

Reaction notes

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