3-Amino-2-pyrazinecarboxylic acid → 3-Amino-pyrazine-2-carboxylic acid methoxy-methylamide

HRID 81476

反応式

HRID 81476 の反応式
[NH2:1][C:2]1[C:3]([C:8]([OH:10])=O)=[N:4][CH:5]=[CH:6][N:7]=1.CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.C(N(C(C)C)CC)(C)C.Cl.[CH3:43][O:44][NH:45][CH3:46]>CN(C=O)C>[CH3:43][O:44][N:45]([CH3:46])[C:8]([C:3]1[C:2]([NH2:1])=[N:7][CH:6]=[CH:5][N:4]=1)=[O:10]

参加物

7

反応物 5

HCID 726563-Amino-2-pyrazinecarboxylic acidHCID 757711-HydroxybenzotriazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

生成物 1

HCID 866345493-Amino-pyrazine-2-carboxylic acid methoxy-methylamide

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 3-aminopyrazine-2-carboxylic acid (1 g, 7.2 mmol) in DMF (15 ml) is added EDC hydrochloride (1.7 g, 8.6 mmol), HOBt (1.16 g, 8.6 mmol), diisopropylethylamine (3.08 ml, 18 mmol) and N-methoxy-N-methylamine hydrochloride (0.84 g, 8.6 mmol), and the resulting solution is stirred at room temperature for 15 hours. The reaction is concentrated in vacuo, and sat. aq. NaHCO3 (50 ml) is added to the residue. The product is extracted into EtOAc (3×60 ml), washed with sat. aq. NaCl (2×50 ml), dried (MgSO4) and concentrated in vacuo to afford a yellow residue. Purification by flash chromatography (SiO2, 0-5% MeOH in DCM) yields 3-amino-pyrazine-2-carboxylic acid methoxy-methylamide as a yellow solid.

後処理

  1. concentrationThe reaction is concentrated in vacuo, and sat. aq. NaHCO3 (50 ml)
  2. additionis added to the residue
  3. extractionThe product is extracted into EtOAc (3×60 ml)
  4. washwashed with sat. aq. NaCl (2×50 ml)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customto afford a yellow residue
  8. customPurification by flash chromatography (SiO2, 0-5% MeOH in DCM)

出典と根拠

ORDレコード
ord-64858c2c746d45169a84ce8da8f2785a
出典データセット
uspto-grants-2014_09
特許番号
US08846687B2

関連ノート

読み込み中…