Piperidine → HCID 178498733, compound

HRID 1297610Notes

Reaction equation

[CH3:1][O:2][C:3]([C:5]1[CH:6]=[N:7][C:8]2[C:13]([C:14]=1[O:15][CH3:16])=[CH:12][C:11]([CH:17]=O)=[CH:10][CH:9]=2)=[O:4].[C:19]1([C@@H:25]2[CH2:27][C@H:26]2[NH:28][C:29]2[S:30][CH2:31][C:32](=[O:34])[N:33]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.N1CCCCC1>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[N:7][C:8]2[C:13]([C:14]=1[O:15][CH3:16])=[CH:12][C:11](/[CH:17]=[C:31]1/[C:32](=[O:34])[N:33]=[C:29]([NH:28][C@@H:26]3[CH2:27][C@H:25]3[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[S:30]/1)=[CH:10][CH:9]=2)=[O:4]

Participants

Conditions

Temperature: 150 °C

Procedure

To the suspension of 6-formyl-4-methoxy-quinoline-3-carboxylic acid methyl ester (example 1e, 100 mg, 0.4 mmol), 2-((1R,2S)-2-phenyl-cyclopropylamino)-thiazol-4-one (example 1f, 93 mg, 0.4 mmol) and benzolic acid (5 mg, 0.04 mmol) in toluene (2 mL) were added and piperidine (5 uL, 0.04 mmol). The mixture was heated to 150° C. by microwave for 20 min. After cooling to room temperature, the solid was collected by filtration, washed with toluene and dried. Flash chromatography (Merck Silica gel 60, 70-230 mesh, 0%-10% methanol in methylene chloride in 30 min) afford 4-methoxy-6-[4-oxo-2-((1R,2S)-2-phenyl-cyclopropylamino)-4H-thiazol-(5Z)-ylidenemethyl]-quinoline-3-carboxylic acid methyl ester (55 mg, 30%) as a light yellow solid. LC-MS m/e 460 (MH+).

Workup

additionwere added
temperatureAfter cooling to room temperature
filtrationthe solid was collected by filtration
washwashed with toluene
customdried

Sources & evidence

ORD record: ord-d826722923db4190a94c0359e842a0fd
Source dataset: uspto-grants-2007_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07250515B2

Reaction notes

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