Piperazine → 2-[2-(5-Methyl-2-Phenyl-Oxazol-4-Yl)-Ethoxy]-6-(1-Piperazinyl)Pyrazine

HRID 1357632Notes

Reaction equation

HRID 1357632 reaction equation
Cl[C:2]1[CH:7]=[N:6][CH:5]=[C:4]([O:8][CH2:9][CH2:10][C:11]2[N:12]=[C:13]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[O:14][C:15]=2[CH3:16])[N:3]=1.CC1OC(C2C=CC=CC=2)=NC=1CCO.[NH:38]1[CH2:43][CH2:42][NH:41][CH2:40][CH2:39]1.C([O-])([O-])=O.[K+].[K+]>>[CH3:16][C:15]1[O:14][C:13]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[N:12][C:11]=1[CH2:10][CH2:9][O:8][C:4]1[CH:5]=[N:6][CH:7]=[C:2]([N:38]2[CH2:43][CH2:42][NH:41][CH2:40][CH2:39]2)[N:3]=1

Participants

5

Reactant 4

HCID 4837PiperazineHCID 11430Potassium CarbonateHCID 7255852-(5-Methyl-2-phenyl-4-oxazolyl)ethanolHCID 181868282-Chloro-6-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]pyrazine

Product 1

HCID 181868852-[2-(5-Methyl-2-Phenyl-Oxazol-4-Yl)-Ethoxy]-6-(1-Piperazinyl)Pyrazine

Procedure

The title compound was prepared according to the procedure of example 50, step 2, starting from 2-chloro-6-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]pyrazine [2.90 g, 9.18 mmol; obtained according to the procedure of example 50, step 1, starting from 2-(5-methyl-2-phenyloxazol-4-yl)ethanol], piperazine (2.37 g, 27.5 mmol) and K2CO3 (1.27 g, 9.19 mmol) with the exception that the final filtration through alumina was omitted. The yield of the of the title compound was 2.09 g (62%) which was obtained as a light yellow oil that solidified when refrigerated. Purity 100% (HPLC). MS m/z 365 (M)+. HRMS m/z calcd for C20H23N5O2 (M)+ 365.1852, found 365.1855.

Workup

  1. customobtained
  2. filtrationfiltration through alumina
  3. customwas obtained as a light yellow oil that solidified when refrigerated

Sources & evidence

ORD record
ord-9f12006a030b4032bc257f996a1f8289
Source dataset
uspto-grants-2003_07
Patent number
US06593330B2

Reaction notes

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