Methanamine, N-methoxy-, hydrochloride (1:1) → 2,6-Dichloro-N-methoxy-N-methylisonicotinamide
Reaction equation
CN([C:4]([O:8][N:9]1N=NC2C=CC=N[C:10]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C1C=NC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[Cl:44][C:45]1[CH:46]=[C:47]([CH:51]=[C:52]([Cl:54])[N:53]=1)[C:48](O)=[O:49].Cl.CNOC>CN(C=O)C>[Cl:44][C:45]1[CH:46]=[C:47]([CH:51]=[C:52]([Cl:54])[N:53]=1)[C:48]([N:9]([O:8][CH3:4])[CH3:10])=[O:49]Participants
7
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
HATU (1.97 g, 5.20 mmol), HOAT (707 mg, 5.20 mmol) and DIEA (1.77 ml, 10.5 mmol) were added to 2,6-dichloroisonicotinic acid (1 g, 5.20 mmol) in anhydrous DMF (5 ml). The mixture was stirred for 5 minutes, then N-methyl methoxylamine hydrochloride (507 mg, 5.20 mmol) was added in one portion followed by DIEA (800 μl, 5.2 mmol). The reaction was stirred for 30 minutes, then the crude product was partitioned between EtOAc (50 ml) and water (50 ml) and the organic level washed with water (3×50 ml). The organic phase was dried over sodium sulphate and concentrated in vacuo. The crude product was purified by flash chromatography eluting with EtOAc:n-hexanes (2:3) to afford the title compound (1.12 g).
Workup
- stirringThe reaction was stirred for 30 minutes
- customthe crude product was partitioned between EtOAc (50 ml) and water (50 ml)
- washthe organic level washed with water (3×50 ml)
- dry with materialThe organic phase was dried over sodium sulphate
- concentrationconcentrated in vacuo
- customThe crude product was purified by flash chromatography
- washeluting with EtOAc:n-hexanes (2:3)
Sources & evidence
- ORD record
- ord-a60786b37dd346d09d0f2f9cd27ff859
- Source dataset
- uspto-grants-2010_05
- Patent number
- US07709503B2
Reaction notes
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