Dipropylamine → 2-(4-Fluorophenyl)-N,N-dipropyl-3H-imidazo[4,5-b]pyridine-3-acetamide

HRID 2351773노트

반응식

HRID 2351773 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:16]([CH2:17][C:18]([OH:20])=O)[C:11]3=[N:12][CH:13]=[CH:14][CH:15]=[C:10]3[N:9]=2)=[CH:4][CH:3]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[CH2:33]([NH:36][CH2:37][CH2:38][CH3:39])[CH2:34][CH3:35]>O1CCCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:16]([CH2:17][C:18]([N:36]([CH2:37][CH2:38][CH3:39])[CH2:33][CH2:34][CH3:35])=[O:20])[C:11]3=[N:12][CH:13]=[CH:14][CH:15]=[C:10]3[N:9]=2)=[CH:6][CH:7]=1

참가 물질

5

반응물 3

HCID 8902DipropylamineHCID 682631,1'-CarbonyldiimidazoleHCID 156171894-fluorophenyl-3H-imidazo[4,5-b]pyridine-3-acetic acid

생성물 1

HCID 143903992-(4-Fluorophenyl)-N,N-dipropyl-3H-imidazo[4,5-b]pyridine-3-acetamide수율 34%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

A mixture of 2-(4-fluorophenyl)-3H-imidazo[4,5-b]pyridine-3-acetic acid (5.0 g, 0.01845 mole) and 1,1'-carbonyldiimidazole (2.99 g, 0.01845 mole) was stirred at room temperature in dry tetrahydrofuran (100 ml) for three hours with a stream of nitrogen bubbling through it. A solution of dipropylamine (5.6 g, 0.0554 mole) in tetrahydrofuran (7 ml) was added and the reaction mixture was refluxed overnight under nitrogen. The solvents were removed under reduced pressure and the residue was triturated in 100 ml of water, the solid was collected by filtration, rinsed twice with water, twice with a 5% potassium hydroxide solution and twice again with water. The solid was dissolved in hot isopropyl alcohol, filtered hot, cooled to room temperature, and water was added to the cloud point. The resulting solid was collected by filtration, rinsed with water, and dried under high vacuum at 42° C. overnight to give 2.22 g (34%) of title compound, mp. 135°-136° C.

후처리

  1. temperaturethe reaction mixture was refluxed overnight under nitrogen
  2. customThe solvents were removed under reduced pressure
  3. customthe residue was triturated in 100 ml of water
  4. filtrationthe solid was collected by filtration
  5. washrinsed twice with water, twice with a 5% potassium hydroxide solution and twice again with water
  6. dissolutionThe solid was dissolved in hot isopropyl alcohol
  7. filtrationfiltered hot
  8. additionwater was added to the cloud point
  9. filtrationThe resulting solid was collected by filtration
  10. washrinsed with water
  11. customdried under high vacuum at 42° C. overnight

출처 및 근거

ORD 기록
ord-e06d09061e0141928b967773f64364b0
출처 데이터셋
uspto-grants-1989_10
특허 번호
US04873251

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