HCID 19592420, compound → HCID 19592513, compound

HRID 613505Notes

Reaction equation

[CH3:1][Mg]Br.[Cl:4][C:5]1[CH:35]=[CH:34][CH:33]=[C:32]([Cl:36])[C:6]=1[C:7]([NH:9][C:10]1[CH:11]=[CH:12][CH:13]=[C:14]2[C:19]=1[N:18]=[CH:17][C:16]([C:20](=[O:25])N(OC)C)=[C:15]2[N:26]1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1)=[O:8]>O1CCCC1>[C:20]([C:16]1[CH:17]=[N:18][C:19]2[C:14]([C:15]=1[N:26]1[CH2:27][CH2:28][O:29][CH2:30][CH2:31]1)=[CH:13][CH:12]=[CH:11][C:10]=2[NH:9][C:7](=[O:8])[C:6]1[C:32]([Cl:36])=[CH:33][CH:34]=[CH:35][C:5]=1[Cl:4])(=[O:25])[CH3:1]

Participants

Conditions

Temperature: 50 °C

Procedure

To a 0.9M solution of methylmagnesium bromide in tetrahydrofuran (1.3 ml) was added dropwise a solution of 8-(2,6-dichlorobenzoylamino)-3-(N-methoxy-N-methylcarbamoyl)-4-morpholinoquinoline (107 mg) in dry tetrahydrofuran (1 ml) with cooling in an ice bath. The mixture was stirred at the same temperature for 1 hour, at ambient temperature for 1 hour, at 50° C. for 2 hours. The mixture was partitioned between ethyl acetate and saturated ammonium chloride aqueous solution. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and evaporated in vacuo. The residue was purified by preparative thin layer chromatography on silica gel. The obtained oil was crystallized from ethanol to give 3-acetyl-8-(2,6-dichlorobenzoylamino)-4-morpholinoquinoline (19 mg) as a white crystal.

Workup

temperaturewith cooling in an ice bath
customThe mixture was partitioned between ethyl acetate and saturated ammonium chloride aqueous solution
washThe organic layer was washed with brine
dry with materialdried over anhydrous magnesium sulfate
customevaporated in vacuo
customThe residue was purified by preparative thin layer chromatography on silica gel
customThe obtained oil was crystallized from ethanol

Sources & evidence

ORD record: ord-1da9b7b1cb3b48a5a96d5f73f1675432
Source dataset: uspto-grants-1999_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06008230

Reaction notes

Loading…