Piperidine → HCID 178467445, compound

HRID 1783627Notes

Reaction equation

HRID 1783627 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][N:5]=1)[CH3:2].[F:16][C:17]1[CH:18]=[C:19]([CH2:23][CH2:24][NH:25][C:26]2[S:27][CH2:28][C:29](=[O:31])[N:30]=2)[CH:20]=[CH:21][CH:22]=1.N1CCCCC1>C(O)C>[CH2:1]([O:3][C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11](/[CH:14]=[C:28]3/[C:29](=[O:31])[N:30]=[C:26]([NH:25][CH2:24][CH2:23][C:19]4[CH:20]=[CH:21][CH:22]=[C:17]([F:16])[CH:18]=4)[S:27]/3)[CH:12]=2)[N:7]=[CH:6][N:5]=1)[CH3:2]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 575906244-Ethoxy-quinazoline-6-carbaldehydeHCID 178516943HCID 178516943, compound

Product 1

HCID 178467445HCID 178467445, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The mixture of 4-ethoxy-quinazoline-6-carbaldehyde (example 10b, 20 mg, 0.1 mmol,), 2-[2-(3-Fluoro-phenyl)-ethylamino]-thiazol-4-one (example 10c, 24 mg, 0.1 mmol) and piperidine (10 ul, 0.1 mmol) in anhydrous ethyl alcohol (1 ml) was microwaved at 160° C. for 25 min. After cooling the reaction to room temperature, the solid was collected by filtration, then washed with MeOH and dried to afford 5-[1-(4-ethoxy-quinazolin-6-yl)-meth-(Z)-ylidene]-2-[2-(3-fluoro-phenyl)-ethylamino]-thiazol-4-one (12 mg, 30%) as light yellow solid. LC-MS m/e 423 (MH+).

Workup

  1. customwas microwaved at 160° C. for 25 min
  2. temperatureAfter cooling
  3. customthe reaction to room temperature
  4. filtrationthe solid was collected by filtration
  5. washwashed with MeOH
  6. customdried

Sources & evidence

ORD record
ord-ac6f378a36264ca09a05c3888f6890ed
Source dataset
uspto-grants-2009_03
Patent number
US07501428B2

Reaction notes

Loading…