Potassium Carbonate → HCID 66873911, compound

HRID 249895Notes

Reaction equation

HRID 249895 reaction equation
Cl[C:2]1[O:3][C:4]2[C:5](=[C:7]([C:11]([O:13][CH3:14])=[O:12])[CH:8]=[CH:9][CH:10]=2)[N:6]=1.[CH3:15][C@@H:16]1[NH:21][CH2:20][CH2:19][NH:18][C:17]1=[O:22].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[CH3:15][C@H:16]1[C:17](=[O:22])[NH:18][CH2:19][CH2:20][N:21]1[C:2]1[O:3][C:4]2[C:5](=[C:7]([C:11]([O:13][CH3:14])=[O:12])[CH:8]=[CH:9][CH:10]=2)[N:6]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 13190462(3S)-3-Methylpiperazin-2-oneHCID 56924368Methyl 2-chlorobenzo[d]oxazole-4-carboxylate

Product 1

HCID 66873911HCID 66873911, compoundYield 98.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of methyl 2-chlorobenzoxazole-4-carboxylate (370 mg, 1.75 mmol), (S)-3-methylpiperazin-2-one (200 mg, 1.75 mmol) and K2CO3 (605 mg, 4.38 mmol), in DMF (15 mL), was stirred at ambient temperature for 17 h. The reaction mixture was diluted with H2O (30 mL) and extracted with CH2Cl2 (2×50 mL). The combined organic layers were washed with H2O (3×20 mL), brine (20 mL), dried (Na2SO4). The material was concentrated under reduced pressure to give (S)-methyl 2-(2-methyl-3-oxopiperazine-1-yl)benzoxazole-4-carboxylate (500 mg, 73%) as a yellow oil. 1H NMR consistent.

Workup

  1. extractionextracted with CH2Cl2 (2×50 mL)
  2. washThe combined organic layers were washed with H2O (3×20 mL), brine (20 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationThe material was concentrated under reduced pressure

Sources & evidence

ORD record
ord-c611bf6ca47b4c0bb49ee8fd41465727
Source dataset
uspto-grants-2011_01
Patent number
US07863271B2

Reaction notes

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