Ammonium Chloride → HCID 67478925, compound
Reaction equation
[CH:1]1([C:4]2[NH:8][N:7]=[C:6]([NH:9][C:10]3[C:15]([N+:16]([O-])=O)=[CH:14][CH:13]=[C:12]([NH:19][C@H:20]([C:22]4[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=4)[CH3:21])[N:11]=3)[CH:5]=2)[CH2:3][CH2:2]1.[Cl-].[NH4+].C([O-])(=O)C.[NH4+]>CO.C1COCC1.[Zn]>[CH:1]1([C:4]2[NH:8][N:7]=[C:6]([NH:9][C:10]3[C:15]([NH2:16])=[CH:14][CH:13]=[C:12]([NH:19][C@H:20]([C:22]4[CH:23]=[CH:24][C:25]([F:28])=[CH:26][CH:27]=4)[CH3:21])[N:11]=3)[CH:5]=2)[CH2:3][CH2:2]1Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 25 °C
Procedure
To a suspension of (S)-N2-(5-cyclopropyl-1H-pyrazol-3-yl)-N6-[1-(4-fluorophenyl)ethyl]-3-nitropyridine-2,6-diamine (Method 12; 0.26 g, 0.68 mmol) and zinc dust (0.223 g, 3.41 mmol) in MeOH:THF (1:1, 12 ml) was slowly added saturated ammonium chloride solution (1.5 ml). The reaction mixture was stirred at 25° C. for 1 hour, to which was then added saturated ammonium acetate solution (5 ml). The resulting mixture was stirred for another 30 minutes. Zn dust was removed by filtration and washed with EtOAc (20 ml). The organic layer was separated, washed with brine (10 ml), dried over Na2SO4, and concentrated. The title compound was used directly for the next step without further purification.
Workup
- stirringThe resulting mixture was stirred for another 30 minutes
- customZn dust was removed by filtration
- washwashed with EtOAc (20 ml)
- customThe organic layer was separated
- washwashed with brine (10 ml)
- dry with materialdried over Na2SO4
- concentrationconcentrated
- customThe title compound was used directly for the next step without further purification
Sources & evidence
- ORD record
- ord-4c19b916daec4cfb9fa8932dd115085f
- Source dataset
- uspto-grants-2012_03
- Patent number
- US08129403B2
Reaction notes
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