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

HRID 30095노트

반응식

HRID 30095 반응식
[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]

참가 물질

8

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

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

후처리

  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

출처 및 근거

ORD 기록
ord-1b00b34e51a549dc9e5341edcc4b3b6e
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07423051B2

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