Triethylamine → 1,5-Dimethyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid (4-benzylamino-6-morpholin-4-yl-pyridin-3-yl)-amide

HRID 930526ノート

反応式

HRID 930526 の反応式
[CH3:1][N:2]1[C:7](=[O:8])[C:6]([CH3:9])=[CH:5][C:4]([C:10]([OH:12])=O)=[CH:3]1.[CH2:13]([NH:20][C:21]1[CH:26]=[C:25]([N:27]2[CH2:32][CH2:31][O:30][CH2:29][CH2:28]2)[N:24]=[CH:23][C:22]=1[NH2:33])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(N(CC)CC)C>C1COCC1>[CH2:13]([NH:20][C:21]1[CH:26]=[C:25]([N:27]2[CH2:28][CH2:29][O:30][CH2:31][CH2:32]2)[N:24]=[CH:23][C:22]=1[NH:33][C:10]([C:4]1[CH:5]=[C:6]([CH3:9])[C:7](=[O:8])[N:2]([CH3:1])[CH:3]=1)=[O:12])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 218859251,5-Dimethyl-6-oxo-1,6-dihydropyridine-3-carboxylic acidHCID 117892051N4-Benzyl-6-morpholin-4-yl-pyridine-3,4-diamine

生成物 1

HCID 1178940391,5-Dimethyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid (4-benzylamino-6-morpholin-4-yl-pyridin-3-yl)-amide

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

N-Propylphosphonic acid anhydride, cyclic trimer (0.356 ml; 0.610 mmol) is added to a mixture of 1,5-dimethyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid D1 (85.000 mg; 0.508 mmol), N4-Benzyl-6-morpholin-4-yl-pyridine-3,4-diamine E-2.3 (133.000 mg; 0.468 mmol) and triethylamine (0.176 ml; 1.271 mmol) in THF (3.000 ml). The reaction mixture is stirred overnight (16 h) at RT. The reaction is quenched with 1M NaOH (2 ml) and diluted with water, then extracted twice with ethyl acetate. The organic layer is dried over Na2SO4 and concentrated in vacuum. The residue is purified on silica chromatography Combiflash (Column: Redisep Rf, 12 g; gradient: DCM/MeOH=100%/0% to 90%/10%; flow rate=30 ml/min; 28 column volumes; detection wavelength: 254 nm). The product containing fractions are combined and concentrated under reduce pressure.

後処理

  1. customThe reaction is quenched with 1M NaOH (2 ml)
  2. additiondiluted with water
  3. extractionextracted twice with ethyl acetate
  4. dry with materialThe organic layer is dried over Na2SO4
  5. concentrationconcentrated in vacuum
  6. customThe residue is purified on silica chromatography Combiflash (Column: Redisep Rf, 12 g; gradient: DCM/MeOH=100%/0% to 90%/10%; flow rate=30 ml/min; 28 column volumes; detection wavelength: 254 nm)
  7. additionThe product containing fractions
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-e4382a4f11e143b3b8db53faf5300f66
出典データセット
uspto-grants-2016_03
特許番号
US09296748B2

反応ノート

読み込み中…