Ammonium Acetate → HCID 178462480, compound
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:16]=[C:17]([F:19])[CH:18]=1)[C:5]([C:7]1[C:8](=[O:15])[N:9]([CH2:13][CH3:14])[CH:10]=[CH:11][CH:12]=1)=O.[NH2:20][C:21]1[CH:25]=[C:24]([NH:26]C(=O)OC(C)(C)C)[NH:23][N:22]=1.C([O-])(=O)C.[NH4+]>>[NH2:26][C:24]1[C:25]2[C:12]3[CH:11]=[CH:10][N:9]([CH2:13][CH3:14])[C:8](=[O:15])[C:7]=3[C:5]([C:4]3[CH:3]=[C:2]([F:1])[CH:18]=[C:17]([F:19])[CH:16]=3)=[N:20][C:21]=2[NH:22][N:23]=1Participants
Procedure
91 mg (0.346 mmol) of 3-(3,5-difluorobenzoyl)-1-ethylpyridin-2(1H)-one with 69 mg (0.346 mmol) of tert-butyl 3-amino-1H-pyrazol-5-ylcarbamate and 533 mg (6.91 mmol) of ammonium acetate are added to a boiling flask. The mixture is carried at 200° C. dry (i.e., without solvent) for 15 minutes. The solution is placed at room temperature, and then the solid is dissolved in a water/ethyl acetate mixture. The phases are separated and the aqueous phase is extracted several times with ethyl acetate. The organic phases are mixed, dried on magnesium sulfate and concentrated. The product is purified by silica gel chromatography (eluent: 10:1 dichloromethane/methanol) to yield 32 mg (27%) of 1-amino-5-(3,5-difluorophenyl)-7-ethyl-3H-pyrazolo[3,4-c][2,7]naphthyridin-6(7H)-one.
Workup
- customis carried at 200° C.
- customdry (i.e., without solvent) for 15 minutes
- customis placed at room temperature
- dissolutionthe solid is dissolved in a water/ethyl acetate mixture
- customThe phases are separated
- extractionthe aqueous phase is extracted several times with ethyl acetate
- additionThe organic phases are mixed
- customdried on magnesium sulfate
- concentrationconcentrated
- customThe product is purified by silica gel chromatography (eluent: 10:1 dichloromethane/methanol)
Sources & evidence
- ORD record
- ord-3441acf690954bc1a62bce1f16bcaf6a
- Source dataset
- uspto-grants-2015_07
- Patent number
- US09085575B2
Reaction notes
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