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

HRID 416570ノート

反応式

HRID 416570 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.) Examples 3-001 to 3-036 were synthesized in similar manner as Example 3-004.

後処理

  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

出典と根拠

ORDレコード
ord-16b25f8737b54bc49af755a4d0fb0ac9
出典データセット
uspto-grants-2012_01
特許番号
US08088924B2

反応ノート

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