Methylamine → HCID 178485280, compound

HRID 1790330Notes

Reaction equation

HRID 1790330 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([C:13]3[CH:18]=[CH:17][N:16]=[C:15]([C:19]([O:21]C)=O)[CH:14]=3)=[CH:11][NH:10][N:9]=2)=[CH:4][CH:3]=1.[CH3:23][NH2:24]>O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:12]([C:13]3[CH:18]=[CH:17][N:16]=[C:15]([C:19]([NH:24][CH3:23])=[O:21])[CH:14]=3)=[CH:11][NH:10][N:9]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 178497299HCID 178497299, compound

Product 1

HCID 178485280HCID 178485280, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of methyl 4-[3-(4-fluorophenyl)-1H-pyrazol-4-yl]-2-pyridinecarboxylate prepared as set forth in Example A-224 (0.45 g, 1.5 mmol) and 20 mL of methylamine (40% aqueous solution) was heated at 120° C. in a sealed tube for 16 hours. After cooling, water was added and the aqueous phase was extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate and filtered. The filtrate was concentrated to afford 0.4 g of 4-[3-(4-fluorophenyl)-1H-pyrazol-4-yl)-N-methyl-2-pyridinecarboxamide as a white solid, mp: 88-89° C. Anal. Calc'd for C16H13FN4O+0.4H2O: C, 63.32; H, 4.58; N, 18.46. Found C, 63.10; H, 4.62; N, 18.35.

Workup

  1. customprepared
  2. temperatureAfter cooling
  3. extractionthe aqueous phase was extracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-48bc566224a84ed6a6938877093be0f6
Source dataset
uspto-grants-2006_07
Patent number
US07071198B1

Reaction notes

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