O-Toluidine → 3-Aminopyrazine-2carboxylic acid o-toluamide

HRID 430513

반응식

HRID 430513 반응식
[NH2:1][C:2]1[C:3]([C:8]([OH:10])=[O:9])=[N:4][CH:5]=[CH:6][N:7]=1.N[C:12]1[C:13](C)=[CH:14]C=[CH:16][CH:17]=1.Cl.C[N:21](C)CCCN=C=NCC>CN(C)C1C=CN=CC=1.C(Cl)Cl>[C:13]1([CH3:14])[C:3]([C:8]([NH2:21])=[O:10])=[CH:2][CH:16]=[CH:17][CH:12]=1.[NH2:1][C:2]1[C:3]([C:8]([OH:10])=[O:9])=[N:4][CH:5]=[CH:6][N:7]=1

참가 물질

6

반응물 3

HCID 7242O-ToluidineHCID 726563-Amino-2-pyrazinecarboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

생성물 1

HCID 697096873-Aminopyrazine-2carboxylic acid o-toluamide

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

실험 절차

A mixture of 3-aminopyrazine carboxylic acid (5.0 g, 35.94 mmol), methylene chloride (110 mL), 4-dimethylaminopyridine (10.98 g, 89.85 mmol), o-toluidine (4.22 mL, 39.53 mmol), and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (8.27 g, 43.13 mmol) was stirred overnight at ambient temperature. The solvent was removed and the residue was diluted with ethyl acetate. This organic phase was extracted with 1N lithium chloride (LiCl), water, and brine, dried over calcium sulfate and concentrated. The residue was flash chromatographed on silica gel (2.75×4 inches) with elution proceeding as follows: hexane (300 mL), nil; 20% ethyl acetate/hexane (500 mL), unweighed recovered o-toluidine; 20% ethyl acetate/hexane (1000 mL) and 30% ethyl acetate/hexane (2000 mL), 4.79 g (58%) of 3-aminopyrazine-2-carboxylic acid o-toluamide as a yellow crystalline solid.

후처리

  1. customThe solvent was removed
  2. additionthe residue was diluted with ethyl acetate
  3. extractionThis organic phase was extracted with 1N lithium chloride (LiCl), water, and brine
  4. dry with materialdried over calcium sulfate
  5. concentrationconcentrated
  6. customchromatographed on silica gel (2.75×4 inches) with elution proceeding
  7. custom20% ethyl acetate/hexane (500 mL), unweighed recovered o-toluidine

출처 및 근거

ORD 기록
ord-30b50b024d454e2f9097c902eda62b64
출처 데이터셋
uspto-grants-2001_11
특허 번호
US06323208B1

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