Triethylamine → 4-(methylamino)-N-[4-(6-methylimidazo[1,2-a]pyridin-2-yl)phenyl]benzamide

HRID 339564

반응식

HRID 339564 반응식
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([C:11]3[CH:17]=[CH:16][C:14]([NH2:15])=[CH:13][CH:12]=3)[N:10]=2)[CH:7]=1.ON1C2C=CC=CC=2N=N1.[CH3:28][NH:29][C:30]1[CH:38]=[CH:37][C:33]([C:34](O)=[O:35])=[CH:32][CH:31]=1.C(N(CC)CC)C>CN(C=O)C>[CH3:28][NH:29][C:30]1[CH:38]=[CH:37][C:33]([C:34]([NH:15][C:14]2[CH:16]=[CH:17][C:11]([C:9]3[N:10]=[C:5]4[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][N:6]4[CH:8]=3)=[CH:12][CH:13]=2)=[O:35])=[CH:32][CH:31]=1

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 663454-(Methylamino)benzoic acidHCID 757711-HydroxybenzotriazoleHCID 8210844-(6-Methylimidazo[1,2-a]pyridin-2-yl)aniline

생성물 1

HCID 583420774-(methylamino)-N-[4-(6-methylimidazo[1,2-a]pyridin-2-yl)phenyl]benzamide수율 33.2%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a stirred solution of 4-(6-methylimidazo[1,2-a]pyridin-2-yl)aniline (0.10 g, 0.448 mmol), 1-hydroxybenzotriazole (0.06 g, 0.448 mmol), 4-methylaminobenzoic acid (0.068 g, 0.448 mmol) and triethylamine (62 μl, 0.045 g, 0.448 mmol) in dry DMF (5 ml) at 0° C. was added 1-ethyl-3-[3-(dimethylaminopropyl]-carbodiimide hydrochloride (0.086 g, 0.448 mmol) under an atmosphere or argon. After 10 min the cooling bath was removed and the reaction mixture was stirred at room temperature for 4 d. The reaction mixture was then added to water (150 ml) with stirring and the precipitate was collected by filtration. Purification by flash chromatography (25:1 DCM/MeOH) gave the title compound (0.053 g, 33%) as an almost colourless solid.

후처리

  1. customAfter 10 min the cooling bath was removed
  2. additionThe reaction mixture was then added to water (150 ml)
  3. stirringwith stirring
  4. filtrationthe precipitate was collected by filtration
  5. customPurification by flash chromatography (25:1 DCM/MeOH)

출처 및 근거

ORD 기록
ord-7e9a0e0620404989977747eea8dccf69
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08895313B2

연결된 노트

불러오는 중…