Pyridinium hydrochloride → HCID 44469657, compound

HRID 2382952Notes

Reaction equation

HRID 2382952 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-8af89f2c8bab4091a55c74e7881bd471
Source dataset
uspto-grants-2012_09
Patent number
US08263597B2

Reaction notes

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