Cyclohexanone → HCID 118598620, compound

HRID 1050382Notes

Reaction equation

[CH:1]1([C:4]([NH:6][C:7]2[CH:12]=[C:11]([NH:13][C:14]3[C:19](=[O:20])[NH:18][C:17]([C:21]([NH2:23])=[O:22])=[C:16]([CH3:24])[N:15]=3)[CH:10]=[CH:9][N:8]=2)=[O:5])[CH2:3][CH2:2]1.[C:25]1(=O)[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1>C(#N)C.[Fe](Cl)(Cl)Cl>[CH3:24][C:16]1[N:15]=[C:14]([NH:13][C:11]2[CH:10]=[CH:9][N:8]=[C:7]([NH:6][C:4]([CH:1]3[CH2:2][CH2:3]3)=[O:5])[CH:12]=2)[C:19](=[O:20])[N:18]2[C:25]3([CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]3)[NH:23][C:21](=[O:22])[C:17]=12

Participants

Conditions

Temperature: 80 °C

Procedure

5-((2-(cyclopropanecarboxamido)pyridin-4-yl)amino)-3-methyl-6-oxo-1,6-dihydropyrazine-2-carboxamide (8, 600 mg, 1.83 mmol) and cyclohexanone (538 mg, 5.48 mmol) were charged in acetonitrile in a 20 mL microwave vial. Iron(III) chloride (889 mg, 1.83 mmol) was added and heated the reaction mixture at 80° C. for 16 h. On completion of the reaction, solvent was removed under vacuum and purified the compound by silica gel (200-400 mesh) column chromatography eluting with 5% methanol in dichloromethane. Appropriate column fractions were concentrated under reduced pressure to afford N-(4-((8′-methyl-1′,5′-dioxo-1′,5′-dihydro-2′H-spiro[cyclohexane-1,3′-imidazo[1,5-a]pyrazin]-6′-yl)amino)pyridin-2-yl)cyclopropanecarboxamide (10, 100 mg, crude) as light brown crude solid which was directly forwarded to next step. MS (ESI) m/z 409.43 [M+1]+.

Workup

customOn completion of the reaction, solvent
customwas removed under vacuum
custompurified the compound by silica gel (200-400 mesh) column chromatography
washeluting with 5% methanol in dichloromethane
concentrationAppropriate column fractions were concentrated under reduced pressure

Sources & evidence

ORD record: ord-72c5d5c774e9497eb37ab09235a33a2f
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09382248B2

Reaction notes

Loading…