Ammonia → 6-(1-Isopropyl-6-oxo-1,6-dihydro-3-pyridazinyl)-3-methoxy-5-phenyl-2-pyrazinecarbonitrile

HRID 915027Notes

Reaction equation

HRID 915027 reaction equation
[CH:1]([N:4]1[C:9](=[O:10])[CH:8]=[CH:7][C:6]([C:11]2[N:12]=[C:13]([C:25]#[N:26])[C:14](C#N)=[N:15][C:16]=2[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[N:5]1)([CH3:3])[CH3:2].N.[CH3:28][OH:29]>>[CH:1]([N:4]1[C:9](=[O:10])[CH:8]=[CH:7][C:6]([C:11]2[N:12]=[C:13]([C:25]#[N:26])[C:14]([O:29][CH3:28])=[N:15][C:16]=2[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[N:5]1)([CH3:2])[CH3:3]

Participants

4

Reactant 3

HCID 222AmmoniaHCID 887MethanolHCID 693333355-(1-Isopropyl-6-oxo-1,6-dihydro-3-pyridazinyl)-6-phenyl-2,3-pyrazinedicarbonitrile

Product 1

HCID 693319586-(1-Isopropyl-6-oxo-1,6-dihydro-3-pyridazinyl)-3-methoxy-5-phenyl-2-pyrazinecarbonitrile

Conditions

Temperature
30 °C

Procedure

A suspension of 5-(1-isopropyl-6-oxo-1,6-dihydro-3-pyridazinyl)-6-phenyl-2,3-pyrazinedicarbonitrile (100 mg) in a 2M solution of ammonia in MeOH (3 ml) was stirred at 25-35° C. for 30 hours in a sealed tube. The mixture was concentrated under reduced pressure and subjected to column chromatography on silica gel eluting with a mixture of n-hexane and EtOAc (60:40 v/v) to give 6-(1-isopropyl-6-oxo-1,6-dihydro-3-pyridazinyl)-3-methoxy-5-phenyl-2-pyrazinecarbonitrile as a solid (32 mg).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. additionsubjected to column chromatography on silica gel eluting with a mixture of n-hexane and EtOAc (60:40 v/v)

Sources & evidence

ORD record
ord-42e8003518d14741808e32f3dd76d68c
Source dataset
uspto-grants-2007_09
Patent number
US07265120B2

Reaction notes

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