Ammonium Acetate → 6-(1-Aminoethyl)-4-chloro-3'-fluoro-3-methylbiphenyl-2-carboxamide
Reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([Cl:21])[C:7]([CH3:20])=[C:8]([C:17]([NH2:19])=[O:18])[C:9]=1[C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=1)(=O)[CH3:2].C([O-])(=O)C.[NH4+].C([BH3-])#[N:28].[Na+]>CO.C(#N)C>[NH2:28][CH:1]([C:4]1[CH:5]=[C:6]([Cl:21])[C:7]([CH3:20])=[C:8]([C:17]([NH2:19])=[O:18])[C:9]=1[C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=1)[CH3:2]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 65 °C
Procedure
A mixture of 6-acetyl-4-chloro-3′-fluoro-3-methylbiphenyl-2-carboxamide (110 mg, 0.34 mmol) and ammonium acetate (270 mg, 3.4 mmol) in methanol (1.9 mL) and acetonitrile (2.0 mL) was heated at 65° C. in a sealed tube for 30 min. The mixture was cooled and sodium cyanoborohydride (43 mg, 0.69 mmol) was added. The reaction was heated at 65° C. for another 4 hours. The mixture was cooled, quenched with saturated sodium bicarbonate, and extracted with dichloromethane. The combined extracts were dried over magnesium sulfate and evaporated to dryness. The residue was used directly in next step (98 mg, 93%). LCMS calculated for C16H17ClFN2O (M+H)+: m/z=307.1. found: 306.9.
Workup
- temperatureThe mixture was cooled
- temperatureThe reaction was heated at 65° C. for another 4 hours
- temperatureThe mixture was cooled
- customquenched with saturated sodium bicarbonate
- extractionextracted with dichloromethane
- dry with materialThe combined extracts were dried over magnesium sulfate
- customevaporated to dryness
Sources & evidence
- ORD record
- ord-30e473a6244e4fdf9fdcee4984ad9262
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09096600B2
Reaction notes
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