Piperidine → HCID 178466956, compound

HRID 1297626Notes

Reaction equation

HRID 1297626 reaction equation
[CH2:1]([O:3][C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([CH:14]=O)[CH:12]=2)[N:7]=[CH:6][C:5]=1[C:16]#[N:17])[CH3:2].[C:18]1([C@@H:24]2[CH2:26][C@H:25]2[NH:27][C:28]2[S:29][CH2:30][C:31](=[O:33])[N:32]=2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.N1CCCCC1>C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11](/[CH:14]=[C:30]3/[C:31](=[O:33])[N:32]=[C:28]([NH:27][C@@H:25]4[CH2:26][C@H:24]4[C:18]4[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=4)[S:29]/3)[CH:12]=2)[N:7]=[CH:6][C:5]=1[C:16]#[N:17])[CH3:2]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 58585818HCID 58585818, compoundHCID 178516947HCID 178516947, compound

Product 1

HCID 178466956HCID 178466956, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
150 °C

Procedure

To the suspension of 4-ethoxy-6-formyl-quinoline-3-carbonitrile (example 14e) (68 mg, 0.3 mmol) and 2-((1R,2S)-2-phenyl-cyclopropylamino)-thiazol-4-one (example 1f, 70 mg, 0.3 mmol) in toluene (2 mL) was added benzolic acid (3.5 mg, 0.03 mmol) and piperidine (35 uL, 0.03 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, 230-400 mesh, 0%-5% methanol in methylene chloride in 30 min) afforded 4-ethoxy-6-[4-oxo-2-((1R,2S)-2-phenyl-cyclopropylamino)-4H-thiazol-(5Z)-ylidenemethyl]-quinoline-3-carbonitrile (35 mg, 27%) as a light yellow solid: LC-MS m/e 441 (MH+).

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationthe solid was collected by filtration
  3. washwashed with toluene
  4. customdried

Sources & evidence

ORD record
ord-0d1335731a4041b5bdf761afe8032780
Source dataset
uspto-grants-2007_07
Patent number
US07250515B2

Reaction notes

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