Water → HCID 59191534, compound

HRID 1479996Notes

Reaction equation

HRID 1479996 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-2ec64fbbebac43c5888b095ad6cf79f4
Source dataset
uspto-grants-2016_08
Patent number
US09409871B2

Reaction notes

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