1,1'-Carbonyldiimidazole → HCID 14390336, 화합물

HRID 621977노트

반응식

HRID 621977 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([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:5]=[CH:6][CH:7]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[CH3:33][NH:34][CH2:35][CH2:36][CH2:37][N:38]1[CH2:43][CH2:42][N:41]([CH3:44])[CH2:40][CH2:39]1>>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[N:16]([CH2:17][C:18]([N:34]([CH3:33])[CH2:35][CH2:36][CH2:37][N:38]3[CH2:39][CH2:40][N:41]([CH3:44])[CH2:42][CH2:43]3)=[O:20])[C:11]3=[N:12][CH:13]=[CH:14][CH:15]=[C:10]3[N:9]=2)[CH:5]=[CH:6][CH:7]=1

참가 물질

4

반응물 3

HCID 682631,1'-CarbonyldiimidazoleHCID 7219854Methyl(3-(4-methylpiperazin-1-yl)propyl)amineHCID 143904542-(3-Chlorophenyl)-3H-imidazo[4,5-b]pyridine-3-acetic acid

생성물 1

HCID 14390336HCID 14390336, 화합물수율 19.8%

실험 절차

Under nitrogen bubbling, a mixture of 2-(3-chlorophenyl)-3H -imidazo[4,5-b]pyridine-3-acetic acid (2.38 g, 0.008 mole) and 1,1'-carbonyldiimidazole (1.34 g, 0.008 mole) was stirred at room temperature for 3 hours. The N,4-dimethyl-1-piperazinepropanamine (1.42 g, 0.008 mole) was added and the reaction mixture was allowed to stir at room temperature for 2 hours. The reaction mixture was evaporated to dryness. The residue was partitioned between methylene chloride and aqueous potassium bicarbonate. The aqueous layer was separated and extracted with methylene chloride. The methylene chloride layers were combined, extracted with aqueous potassium bicarbonate and water and dried over sodium sulfate. The filtrate was evaporated and the solid residue was recrystallized as a fumarate salt from ethyl alcohol-isopropyl ether. Recrystallization from isopropyl alcohol-acetonitrile-isopropyl ether did not improve the analysis. The solid was converted to the free base. The free base was treated with boiling hexanes and allowed to cool to room temperature. The solid was collected by filtration, washed with hexane, and dried under high vacuum overnight to give 0.7 g of title compound, mp 114°-17° C.

후처리

  1. stirringto stir at room temperature for 2 hours
  2. customThe reaction mixture was evaporated to dryness
  3. customThe residue was partitioned between methylene chloride and aqueous potassium bicarbonate
  4. customThe aqueous layer was separated
  5. extractionextracted with methylene chloride
  6. extractionextracted with aqueous potassium bicarbonate and water
  7. dry with materialdried over sodium sulfate
  8. customThe filtrate was evaporated
  9. customthe solid residue was recrystallized as a fumarate salt from ethyl alcohol-isopropyl ether
  10. customRecrystallization from isopropyl alcohol-acetonitrile-isopropyl ether
  11. additionThe free base was treated with boiling hexanes
  12. temperatureto cool to room temperature
  13. filtrationThe solid was collected by filtration
  14. washwashed with hexane
  15. customdried under high vacuum overnight

출처 및 근거

ORD 기록
ord-ecc311453247478b9cca5167961730a1
출처 데이터셋
uspto-grants-1989_04
특허 번호
US04824951

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