1-Methyl-3-aminopyrazole → HCID 86689721, compound

HRID 1396352Notes

Reaction equation

HRID 1396352 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:6]=[N:7][C:8]([Cl:12])=[CH:9][C:10]=1Cl)=[O:4].[CH3:13][N:14]1[CH:18]=[CH:17][C:16]([NH2:19])=[N:15]1>CN1CCCC1=O>[CH3:1][O:2][C:3]([C:5]1[N:6]=[N:7][C:8]([Cl:12])=[CH:9][C:10]=1[NH:19][C:16]1[CH:17]=[CH:18][N:14]([CH3:13])[N:15]=1)=[O:4]

Participants

4

Reactant 2

HCID 1372541-Methyl-3-aminopyrazoleHCID 17848322Methyl 4,6-dichloropyridazine-3-carboxylate

Product 1

HCID 86689721HCID 86689721, compoundYield 32.2%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
110 °C

Procedure

4,6-Dichloro-pyridazine-3-carboxylic acid methyl ester (165 mg, 0.8 mmol) and 1-methyl-1H-pyrazol-3-amine (81 mg, 0.837 mmol) were dissolved in of N-methylpyrrolidinone (3.2 mL). The reaction was heated at 110° C. for 2 h, then cooled and concentrated in vacuo. The residue was diluted with water and then extracted with ethyl acetate. The combined organic extracts were washed with brine, dried (sodium sulfate), filtered and concentrated in vacuo. Purification by chromatography (silica, 10 to 70% ethyl acetate in hexanes) gave 6-chloro-4-(1-methyl-1H-pyrazol-3-ylamino)-pyridazine-3-carboxylic acid methyl ester (69 mg, 32%) as a light brown solid. 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 10.09 (br. s., 1H) 8.24 (s, 1H) 7.34 (d, J=2.3 Hz, 1H) 6.02 (d, J=2.3 Hz, 1H) 4.08 (s, 3H) 3.91 (s, 3H); LCMS (EI/CI) m/z: 268 [M+H].

Workup

  1. temperaturecooled
  2. concentrationconcentrated in vacuo
  3. additionThe residue was diluted with water
  4. extractionextracted with ethyl acetate
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried (sodium sulfate)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customPurification by chromatography (silica, 10 to 70% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-2b1ff0b55b2d4265b8cfa70f5805a30e
Source dataset
uspto-grants-2014_12
Patent number
US08901124B2

Reaction notes

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