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

HRID 2170306

反応式

HRID 2170306 の反応式
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]

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-09ae41a2569b4559a9b8ed40f4786d39
出典データセット
uspto-grants-2015_06
特許番号
US09050344B2

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