HCID 18358856, compound → HCID 178520047, compound

HRID 1954744Notes

Reaction equation

HRID 1954744 reaction equation
COC1C=CC(C[N:10]2[C:14]3[C:15](=[O:26])[NH:16][C:17]4[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:18]=4[C:19](=[O:20])[C:13]=3[C:12]([CH:27]=[O:28])=[N:11]2)=CC=1.COC1C=CC(CN2C(C=O)=C3C(C(=O)NC4C=C(Cl)C=CC=4C3=O)=N2)=CC=1>C(#N)C.O>[Cl:25][C:23]1[CH:22]=[CH:21][C:18]2[C:19](=[O:20])[C:13]3[C:12]([CH:27]=[O:28])=[N:11][NH:10][C:14]=3[C:15](=[O:26])[NH:16][C:17]=2[CH:24]=1

Participants

5

Reactant 2

HCID 18358856HCID 18358856, compoundHCID 18358913HCID 18358913, compound

Product 1

HCID 178520047HCID 178520047, compoundYield 9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of 1-(4-methoxyphenylmethyl)-7-chloro-3-formylpyrazolo[3,4-c][1]benzazepine-4,10(1H,9H)-dione or 2-(4-methoxyphenylmethyl)-7-chloro-3-formylpyrazolo[3,4-c][1]benzazepine-4,10(2H,9H)-dione from Example 20(b) above (400 mg, 1.01 mmol) and ceric ammonium nitrate (2.2 g, 4.03 mmol) in a mixture of acetonitrile (12 mL) and water (4 mL) was stirred for 17 hours at room temperature and filtered. The isolated solid was washed with a mixture of acetonitrile (12 mL) and water (4 mL) followed by acetone (10 mL). The acetonitrile-water solutions were extracted with ethyl acetate. The solid material from above was combined with the ethyl acetate extract and solvent was removed by rotary evaporation. The residue was washed with hot methanol (1×20 mL then 1×10 mL) and dried to give the title compound (25 mg, 9%).

Workup

  1. filtrationfiltered
  2. washThe isolated solid was washed with a mixture of acetonitrile (12 mL) and water (4 mL)
  3. extractionThe acetonitrile-water solutions were extracted with ethyl acetate
  4. extractionextract
  5. customsolvent was removed by rotary evaporation
  6. washThe residue was washed with hot methanol (1×20 mL
  7. custom1×10 mL) and dried

Sources & evidence

ORD record
ord-23b6947205b54b21a2f1df8120ed5fee
Source dataset
uspto-grants-2000_09
Patent number
US06124281

Reaction notes

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