Pyridinium hydrochloride → HCID 44469657, compound

HRID 1677698Notes

Reaction equation

HRID 1677698 reaction equation
C[O:2][C:3]1[CH:8]=[C:7]([CH2:9][NH:10][C:11]([C:13]2[C:14]3[CH:15]=[N:16][N:17]([C:22]4[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=4)[C:18]=3[CH:19]=[CH:20][CH:21]=2)=[O:12])[CH:6]=[CH:5][N:4]=1.Cl.[NH+]1C=CC=CC=1>C(OCC)(=O)C.O>[O:2]=[C:3]1[CH:8]=[C:7]([CH2:9][NH:10][C:11]([C:13]2[C:14]3[CH:15]=[N:16][N:17]([C:22]4[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=4)[C:18]=3[CH:19]=[CH:20][CH:21]=2)=[O:12])[CH:6]=[CH:5][NH:4]1

Participants

5

Reactant 2

HCID 21584435Pyridinium hydrochlorideHCID 58138846HCID 58138846, compound

Product 1

HCID 44469657HCID 44469657, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-(4-Fluoro-phenyl)-1H-indazole-4-carboxylic acid (2-methoxy-pyridin-4-ylmethyl)-amide (38 mg, 0.10 mmol) and pyridinium hydrochloride (117 mg, 1.01 mmol) were heated to 125° C. in a sealed tube. After 10 minutes, the mixture was cooled to room temperature and diluted with ethyl acetate (3 mL) and water (3 mL). The organic layer was washed with water (3×3 mL) and concentrated at 45° C. under a stream of nitrogen. The residue was dissolved in CH2Cl2 (3 mL) and concentrated (repeated 3 times). The solid was triturated with ether (3 mL), filtered and air dried to afford the title compound as a white solid.

Workup

  1. washThe organic layer was washed with water (3×3 mL)
  2. concentrationconcentrated at 45° C. under a stream of nitrogen
  3. dissolutionThe residue was dissolved in CH2Cl2 (3 mL)
  4. concentrationconcentrated (repeated 3 times)
  5. customThe solid was triturated with ether (3 mL)
  6. filtrationfiltered
  7. customair dried

Sources & evidence

ORD record
ord-634ee8f8580e4b84a5999e2e104e6845
Source dataset
uspto-grants-2011_08
Patent number
US08008327B2

Reaction notes

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