Ammonium Chloride → HCID 89689976, compound

HRID 517932Notes

Reaction equation

[O:1]=[C:2]1[C:11]2[C:6](=[N:7][C:8]([C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=3)=[C:9]([C:12]3[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=3)[N:10]=2)[N:5]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:4][CH2:3]1.[CH3:33][Mg+].[Br-].[Cl-].[NH4+]>C1COCC1>[OH:1][C:2]1([CH3:33])[C:11]2[C:6](=[N:7][C:8]([C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=3)=[C:9]([C:12]3[CH:13]=[CH:14][C:15]([CH3:18])=[CH:16][CH:17]=3)[N:10]=2)[N:5]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:4][CH2:3]1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of tert-butyl 8-oxo-2,3-di-p-tolyl-7,8-dihydropyrido[2,3-b]pyrazine-5(6H)-carboxylate (step 2) (591 mg, 1.376 mmol) in THF (20 ml) at 0° C. was added 1M MeMgBr in THF (5.50 ml, 5.50 mmol). The mixture was left to stir at 0° C. for 30 mins under an atmosphere of nitrogen and then warmed to room temperature. After 1.5 hours, the reaction mixture was poured into a saturated ammonium chloride solution (30 ml). The product was extracted with ethyl acetate (2×30 ml) and the combined organic extracts were dried over MgSO4, filtered and concentrated under reduced pressure to give the crude product as an oil. Purification of the oil by chromatography on silica eluting with EtOAc in iso-hexane afforded the titled compound;

Workup

waitThe mixture was left
temperaturewarmed to room temperature
waitAfter 1.5 hours
extractionThe product was extracted with ethyl acetate (2×30 ml)
dry with materialthe combined organic extracts were dried over MgSO4
filtrationfiltered
concentrationconcentrated under reduced pressure
customto give the crude product as an oil
customPurification of the oil by chromatography on silica eluting with EtOAc in iso-hexane

Sources & evidence

ORD record: ord-da6813f964a341a7b002fb6c7ba254bf
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09115129B2

Reaction notes

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