Water → HCID 59191534, compound

HRID 447118Notes

Reaction equation

HRID 447118 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:6]=[CH:7][C:8]([N:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)=[N:9][CH:10]=1)=[O:4].[Cl:17][C:18]1[N:19]=[N:20][C:21](Cl)=[C:22]([CH3:25])[C:23]=1[CH3:24].O>CN1C(=O)CCC1>[CH3:1][O:2][C:3]([C:5]1[N:6]=[CH:7][C:8]([N:11]2[CH2:12][CH2:13][N:14]([C:21]3[N:20]=[N:19][C:18]([Cl:17])=[C:23]([CH3:24])[C:22]=3[CH3:25])[CH2:15][CH2:16]2)=[N:9][CH:10]=1)=[O:4]

Participants

5

Reactant 3

HCID 962WaterHCID 211875053,6-Dichloro-4,5-dimethylpyridazineHCID 67176889HCID 67176889, compound

Product 1

HCID 59191534HCID 59191534, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
190 °C

Procedure

To the solution of 3,4,5,6-tetrahydro-2H-[1,2]bipyrazinyl-5′-carboxylic acid methyl ester (250 mg, 1.07 mmol) in NMP (5 mL) is added 3,6-dichloro-4,5-dimethyl-pyridazine (237 mg, 1.33 mmol) and TEA (446 μl, 3.21 mmol), the reaction mixture is stirred at 190° C. for 60 min. Water is added to the mixture and extracted with EtOAc. The combined organic layers are washed with water, brine, dried over Na2SO4, filtered and concentrated. The crude product is purified by HPLC, (acetonitrile/water: 10%˜95% with 3% 1-propanol) to give white powder (165 mg, 43%).

Workup

  1. extractionextracted with EtOAc
  2. washThe combined organic layers are washed with water, brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product is purified by HPLC, (acetonitrile/water: 10%˜95% with 3% 1-propanol)

Sources & evidence

ORD record
ord-72642674d96340b68ee790b5bf161c37
Source dataset
uspto-grants-2013_07
Patent number
US08481542B2

Reaction notes

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