1,1'-Carbonyldiimidazole → HCID 23037392, 화합물

HRID 2073065노트

반응식

HRID 2073065 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:16]([CH2:17][C:18]([OH:20])=[O:19])[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.[NH2:33][CH:34]1[CH2:38][N:37]([CH2:39][CH3:40])[N:36]([CH2:41][CH3:42])[CH2:35]1>O1CCCC1>[OH2:19].[ClH:1].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:16]([CH2:17][C:18]([NH:33][CH:34]3[CH2:38][N:37]([CH2:39][CH3:40])[N:36]([CH2:41][CH3:42])[CH2:35]3)=[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 682631,1'-CarbonyldiimidazoleHCID 5591991,2-Diethyl-4-pyrazolidinamineHCID 143904574-chlorophenyl-3H-imidazo[4,5-b]pyridine-3-acetic acid

생성물 1

HCID 23037392HCID 23037392, 화합물수율 118%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

A suspension of 2-(4-chlorophenyl)-3H-imidazo[4,5-b]pyridine-3-acetic acid (5.0 g, 0.0174 mole), 1,1'carbonyldiimidazole (2.82 g, 0.0174 mole) and dry tetrahydrofuran (100 ml) was stirred at room temperature for two hours with nitrogen bubbling through it. A solution of 4-amino-1,2-diethyl-pyrazolidine (7.5 g, 0.0522 mole) in tetrahydrofuran (6 ml) was added and the reaction mixture was stirred at room temperature overnight under nitrogen. The reaction mixture was evaporated under reduced pressure to an oil. Water (200 ml) was added, and the resulting suspension was stirred. The solid was collected by filtration, rinsed twice with water, twice with 5% potassium hydroxide solution and twice again with water. The solid was dissolved in hot isopropyl alcohol, filtered hot, and acidified with hydrogen chloride in isopropyl alcohol. Isopropyl ether was added to the cloud point, and upon cooling to room temperature, a solid precipitated. The solid was collected by filtration, rinsed with isopropyl ether, and dried under high vacuum to give 4.8 g (56%) of title compound, mp 220° C. (darkens), 228°-230° C. (melts).

후처리

  1. stirringthe reaction mixture was stirred at room temperature overnight under nitrogen
  2. customThe reaction mixture was evaporated under reduced pressure to an oil
  3. additionWater (200 ml) was added
  4. stirringthe resulting suspension was stirred
  5. filtrationThe solid was collected by filtration
  6. washrinsed twice with water, twice with 5% potassium hydroxide solution and twice again with water
  7. dissolutionThe solid was dissolved in hot isopropyl alcohol
  8. filtrationfiltered hot
  9. additionIsopropyl ether was added to the cloud point
  10. temperatureupon cooling to room temperature
  11. customa solid precipitated
  12. filtrationThe solid was collected by filtration
  13. washrinsed with isopropyl ether
  14. customdried under high vacuum

출처 및 근거

ORD 기록
ord-75258a26f3c54852bd9b4c842bfe3ef1
출처 데이터셋
uspto-grants-1990_04
특허 번호
US04914109

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