HCID 18698776, compound → HCID 18698784, compound

HRID 2289638Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[N:10]=[CH:11][N:12](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH:13]=2)=[CH:4][CH:3]=1.[Cl:33][C:34]1[N:39]=[C:38]([N:40]2[CH:45]=[CH:44][C:43]([CH2:46]N3C(CC4C=CC(C#N)=CC=4)=CN=C3)=[CH:42][C:41]2=[O:61])[CH:37]=[N:36][CH:35]=1>C(#N)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][C:9]2[N:10]([CH2:46][C:43]3[CH:44]=[CH:45][N:40]([C:38]4[CH:37]=[N:36][CH:35]=[C:34]([Cl:33])[N:39]=4)[C:41](=[O:61])[CH:42]=3)[CH:11]=[N:12][CH:13]=2)=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 4-(4-bromophenyloxy)-1-trityl-1H-imidazole (0.164 g, 0.34 mmol) and 4-bromomethyl-1-(6-chloro-pyrazin-2-yl)-1H-pyridin-2-one from example 7 (98.5 mg, 0.34 mmol) in anhydrous acetonitrile (10 mL) was heated under reflux at 60° C. for 24 h. The resultant solution was concentrated, and the residue dissolved in a mixture of methanol (10 mL) and 1,2-dichloroethane (1 mL). The solution was heated under reflux for 2 h, and concentrated under vacuum. The residue was subjected to column chromatography on silica gel eluting with 1:1 v/v 6% methanol in chloroform and chloroform saturated with ammonia gas. Collection and concentration of appropriate fractions provided the titled compound.

Workup

temperaturewas heated
concentrationThe resultant solution was concentrated
dissolutionthe residue dissolved in a mixture of methanol (10 mL) and 1,2-dichloroethane (1 mL)
temperatureThe solution was heated
temperatureunder reflux for 2 h
concentrationconcentrated under vacuum
customCollection and concentration of appropriate fractions

Sources & evidence

ORD record: ord-76252b0eb5a54228babb7271225eba3f
Source dataset: uspto-grants-2000_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06093737

Reaction notes

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