Methanamine, N-methoxy-, hydrochloride (1:1) → 6-acetamido-3-bromo-N-methoxy-N-methylpicolinamide

HRID 2170306

반응식

HRID 2170306 반응식
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.[C:25]([NH:28][C:29]1[N:34]=[C:33]([C:35]([OH:37])=O)[C:32]([Br:38])=[CH:31][CH:30]=1)(=[O:27])[CH3:26].C(N(CC)C(C)C)(C)C.Cl.CNOC>ClCCl>[C:25]([NH:28][C:29]1[N:34]=[C:33]([C:35]([N:9]([O:8][CH3:4])[CH3:10])=[O:37])[C:32]([Br:38])=[CH:31][CH:30]=1)(=[O:27])[CH3:26]

참가 물질

6

반응물 4

HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 253069883-Bromo-6-acetamidopyridine-2-carboxylic acid

생성물 1

HCID 902804776-acetamido-3-bromo-N-methoxy-N-methylpicolinamide

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

HATU (1-[Bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate) (4.56 g, 12.0 mmol) was added to a solution of 6-acetamido-3-bromopicolinic acid (2.6 g, 10.0 mmol) and DIPEA (N,N-diisopropylethylamine)(5.2 ml, 30 mmol) in DCM (dichloromethane)(10 ml). After 10 minutes, N,O-dimethylhydroxylamine hydrochloride (1.5 g, 15.0 mmol) was added to the reaction. The reaction was stirred at room temperature for 5 min. The reaction mixture was partitioned between EtOAc (ethyl acetate) and saturated NH4Cl solution. The organic phase was washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The crude material was used in the next step without further purification. MS (m/z) 302.1 [M+H]+. 1H NMR (400 MHz, cd3cl) δ 8.14 (s, 1H), 8.13 (d, J=8.4 Hz, 1H), 7.85 (d, J=8.4 Hz, 1H), 3.56 (s, 3H), 3.37 (s, 3H), 2.20 (s, 3H).

후처리

  1. customThe reaction mixture was partitioned between EtOAc (ethyl acetate) and saturated NH4Cl solution
  2. washThe organic phase was washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude material was used in the next step without further purification

출처 및 근거

ORD 기록
ord-09ae41a2569b4559a9b8ed40f4786d39
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09050344B2

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