N-methyl-2-pyrrolidone → 3-Benzoyl-7-chloropyrazolo[3,4-c][1]benzazepine-4,10(1H,9H)-dione
Reaction equation
[Cl:1][C:2]1[CH:27]=[CH:26][C:5]([C:6]([C:8]2[C:9]([C:18](=[O:25])[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[N:10][NH:11][C:12]=2[C:13]([O:15]CC)=O)=[O:7])=[C:4]([NH2:28])[CH:3]=1.CN1CCCC1=O.C([O-])(=O)C.[NH4+]>O>[C:18]([C:9]1[C:8]2[C:6](=[O:7])[C:5]3[CH:26]=[CH:27][C:2]([Cl:1])=[CH:3][C:4]=3[NH:28][C:13](=[O:15])[C:12]=2[NH:11][N:10]=1)(=[O:25])[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 160 °C
Procedure
A solution of ethyl 4-(4-chloro-2-aminobenzoyl)-3-benzoyl-1H-pyrazole-5-carboxylate (620 mg, 1.56 mmol), 1-methyl-2-pyrrolidinone (4 mL) and ammonium acetate (120 mg, 1.56 mmol) was heated at 146° C. for 16.5 hours. The temperature was increased to 160° C. for 1 hour. The solution was allowed to cool to room temperature and water (60 mL) was added. The insoluble material (468 mg) was filtered, dried, and twice subjected to flash chromatography eluting with hexanes:ethyl acetate (90:10-50:50) to give impure product. The crude solid was triturated with ethanol (15 mL), washed with ethanol (3×10 mL) and dried to give the title compound (30.5 mg, 5.6% yield, m.p. 370-373° C. dec.).
Workup
- temperatureto cool to room temperature
- filtrationThe insoluble material (468 mg) was filtered
- customdried
- washeluting with hexanes:ethyl acetate (90:10-50:50)
- customto give impure product
- customThe crude solid was triturated with ethanol (15 mL)
- washwashed with ethanol (3×10 mL)
- customdried
Sources & evidence
- ORD record
- ord-766dad4bdd81449e807156f85a9550b9
- Source dataset
- uspto-grants-2001_11
- Patent number
- US06313290B1
Reaction notes
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