Benzylamine → 1-Ethyl-2-oxo-5,6-dimethyl-1,2-dihydropyridine-3-carboxylic acid benzylamide

HRID 489279노트

반응식

HRID 489279 반응식
[CH2:1]([N:3]1[C:8]([CH3:9])=[C:7]([CH3:10])[CH:6]=[C:5]([C:11]([OH:13])=O)[C:4]1=[O:14])[CH3:2].[CH2:15]([NH2:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(N(C(C)C)CC)(C)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N2CCCC2)(N2CCCC2)N2CCCC2)C2C=CC=CC=2N=N1>CN(C=O)C.C(OCC)(=O)C>[CH2:15]([NH:22][C:11]([C:5]1[C:4](=[O:14])[N:3]([CH2:1][CH3:2])[C:8]([CH3:9])=[C:7]([CH3:10])[CH:6]=1)=[O:13])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

참가 물질

7

반응물 4

HCID 7504BenzylamineHCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 222665051-Ethyl-3-carboxy-5,6-dimethyl-2-pyridone

생성물 1

HCID 235880331-Ethyl-2-oxo-5,6-dimethyl-1,2-dihydropyridine-3-carboxylic acid benzylamide수율 91.1%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

1-Ethyl-3-carboxy-5,6-dimethyl-2-pyridone (3-003-04) (195 mg) was dissolved in DMF (3 mL), and to the reaction mixture were added benzylamine (0.17 mL), diisopropylethylamine (0.35 mL), and benzotriazol-1-yloxytripyrrolidinophosphonium hexafluorophosphate (PyBOP, 624 mg), and the reaction mixture was stirred at room temperature for 1 h. The reaction mixture was diluted with ethyl acetate, washed twice with hydrochloric acid and aqueous sodium bicarbonate solution, respectively, and water, dried over magnesium sulfate, and evaporated under reduced pressure. The residue (0.40 g) was subjected to silica gel (30 g) column chromatography (chloroform) to give 1-ethyl-2-oxo-5,6-dimethyl-1,2-dihydropyridine-3-carboxylic acid benzylamide (3-003) (259 mg, 91.1%) as a crystal, followed by recrystallization from methylene/n-hexane to give colorless needle crystal (207 mg, 72.9%, m.p. 117° C.)

후처리

  1. washwashed twice with hydrochloric acid and aqueous sodium bicarbonate solution
  2. dry with materialrespectively, and water, dried over magnesium sulfate
  3. customevaporated under reduced pressure

출처 및 근거

ORD 기록
ord-87e9b8d2408149f0858c5c1486ef08f6
출처 데이터셋
uspto-grants-2005_12
특허 번호
US06977266B2

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