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

HRID 81476

반응식

HRID 81476 반응식
[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]

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-64858c2c746d45169a84ce8da8f2785a
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846687B2

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