Water → HCID 178434581, compound

HRID 719260Notes

Reaction equation

HRID 719260 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.[CH3:10][C:11]1[C:15]([NH2:16])=[C:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[NH:13][N:12]=1.O>N1C=CC=CC=1>[CH3:10][C:11]1[C:15]([NH:16][C:1](=[O:8])[C:2]2[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=2)=[C:14]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[NH:13][N:12]=1

Participants

5

Reactant 3

HCID 962WaterHCID 417436Pyridine-4-carbonyl chlorideHCID 178434570HCID 178434570, compound

Product 1

HCID 178434581HCID 178434581, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

205 mg of isonicotinoyl chloride*HCl were added to a solution of 200 mg of 3-methyl-5-phenyl-1H-pyrazol-4-ylamine in 2 ml of pyridine and the mixture was then stirred at RT for 12 h; water was then added and the whole was extracted with methylene chloride. The organic phase was dried over magnesium sulfate, concentrated under reduced pressure and purified by means of HPLC (Merk-Hibar-Lichrospher 100-RP-18, water (0.1% trifluoroacetic acid)/acetonitrile (0.1% trifluoroacetic acid)=80/20→10/90). The following was obtained: 27. C16H14N4O (278.32); MS (ESI) 279 (M+H)

Workup

  1. extractionthe whole was extracted with methylene chloride
  2. dry with materialThe organic phase was dried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. custompurified by means of HPLC (Merk-Hibar-Lichrospher 100-RP-18, water (0.1% trifluoroacetic acid)/acetonitrile (0.1% trifluoroacetic acid)=80/20→10/90)
  5. customThe following was obtained

Sources & evidence

ORD record
ord-7927c995f5e84c6895ec1052ff1e5d8e
Source dataset
uspto-grants-2006_11
Patent number
US07132428B2

Reaction notes

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