Isopropanol → HCID 178462036, compound

Reaction equation

[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([NH:7][C:8](=[N:16][C:17]#[N:18])OC2C=CC=CC=2)[CH:2]=1.[CH3:19][C@@H:20]([NH2:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(O)(C)C>CO>[C:17]([N:16]=[C:8]([NH:27][C@@H:20]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH3:19])[NH:7][C:3]1[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=1)#[N:18]

Participants

Procedure

A stirred mixture of N-(3-pyridyl)-N'-cyano-O-phenylisourea (see, Example 5 for procedure) (8.00 g, 0.336 mmol), (R)-α-methylbenzylamine (10.8 mL, 0.0835 mol) and isopropanol (53.3 mL) was refluxed, under nitrogen, for 4 hours. The reaction was complete by TLC with 10% MeOH-1% NH4OH-CHCl3. The mixture was concentrated in vacuo. The residue was mixed with EtOAc several times with concentration after each addition; the resulting solid was triturated with hot EtOAc, collected by filtration and recrystallized from MeOH-CH2Cl2 -EtOAc to give 6.6 g of product: mp 185°-187° C.