Methanamine, N-methoxy-, hydrochloride (1:1) → 2,6-Dichloro-N-methoxy-N-methylpyridine-3-carboxamide

HRID 30095

反応式

HRID 30095 の反応式
[Cl:1][C:2]1[N:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].F[P-](F)(F)(F)(F)F.[N:19]1([O:28][C:29](N(C)C)=[N+](C)C)[C:23]2C=CC=CC=2N=N1.O.ON1C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.Cl.CNOC>CN(C)C=O.O>[Cl:1][C:2]1[N:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4]([N:19]([O:28][CH3:29])[CH3:23])=[O:5]

参加物

8

反応物 5

HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 81531DiisopropylethylamineHCID 8540472,6-Dichloronicotinic acidHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 27960291-Hydroxybenzotriazole hydrate

生成物 1

HCID 534034112,6-Dichloro-N-methoxy-N-methylpyridine-3-carboxamide収率 50%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 2,6-dichloronicotinic acid (500 mg, 2.63 mmol, Aldrich 90%) in anhydrous N,N-dimethylformamide (5 mL) were added O-benzotriazol-1-yl-N,N,N′,N′-tetramethyluronium hexafluorophosphate (1.28 g, 3.37 mmol, Aldrich), 1-hydroxybenzotriazole hydrate (456 mg, 3.37 mmol, Aldrich) followed by N,N-diisopropylethylamine (1.3 g, 10.0 mmol) and N,O-dimethylhydroxylamine hydrochloride (306 mg, 3.15 mmol, Aldrich) at 0° C. The reaction was stirred for 1-2 hrs, treated with water and extracted with ethyl acetate. The combined organic extracts were washed with brine, dried and concentrated. The crude product was purified on silica gel with hexanes/ethyl acetate to give 2,6-Dichloro-N-methoxy-N-methyl-nicotinamide as a white solid (304.5 mg, 50% yield). HRMS, observed: 233.9968, Calcd for M+: 233.9963

後処理

  1. extractionextracted with ethyl acetate
  2. washThe combined organic extracts were washed with brine
  3. customdried
  4. concentrationconcentrated
  5. customThe crude product was purified on silica gel with hexanes/ethyl acetate

出典と根拠

ORDレコード
ord-1b00b34e51a549dc9e5341edcc4b3b6e
出典データセット
uspto-grants-2008_09
特許番号
US07423051B2

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