Methanamine, N-methoxy-, hydrochloride (1:1) → N-methoxy-N,1-dimethyl-1H-imidazole-2-carboxamide

HRID 1988636ノート

反応式

HRID 1988636 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.[CH3:25][N:26]1[CH:30]=[CH:29][N:28]=[C:27]1[C:31]([OH:33])=O.Cl.CNOC.C(N(C(C)C)CC)(C)C>CN(C=O)C>[CH3:10][N:9]([O:8][CH3:4])[C:31]([C:27]1[N:26]([CH3:25])[CH:30]=[CH:29][N:28]=1)=[O:33]

参加物

6

反応物 4

HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 81531DiisopropylethylamineHCID 5576781-methyl-1H-imidazole-2-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

生成物 1

HCID 57762806N-methoxy-N,1-dimethyl-1H-imidazole-2-carboxamide収率 212.1%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

HATU (O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate) (1.75 g; 4.60 mmol) was added in on portion to a stirring solution of 1-methyl-1H-imidazole-2-carboxylic acid (509 mg; 4.04 mmol), N,O-dimethylhydroxylamine hydrochloride (391 mg; 4.01 mmol), and diisopropylethylamine (2.0 mL; 11.9 mmol) in anhydrous DMF (14 mL). The mixture was stirred at room temperature for 17 hours and partitioned between ethyl acetate (100 mL) and water (100 mL). The organic phase was dried (MgSO4) and concentrated in vacuo, giving a colourless oil (1.45 g). This was purified by column chromatography, giving the title compound as a colourless oil (494 mg; 73%).

後処理

  1. custompartitioned between ethyl acetate (100 mL) and water (100 mL)
  2. dry with materialThe organic phase was dried (MgSO4)
  3. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-78e47bdf5a66474fb8f1a6dbc38b81c2
出典データセット
uspto-grants-2010_01
特許番号
US07642256B2

反応ノート

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