1,1'-Carbonyldiimidazole → 2-(3-Chlorophenyl)-N-(1-ethyl-2-pyrrolidinylmethyl)-3H-imidazo [4,5-b]pyridine-3-acetamide hydrochloride

HRID 623001

반응식

HRID 623001 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)([N:23]1C=CN=C1)=O.NC[CH2:35][CH:36]1[CH2:40][CH2:39][CH2:38][N:37]1[CH2:41][CH3:42]>O1CCCC1>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[N:16]([CH2:17][C:18]([NH:23][CH2:35][CH:36]3[CH2:40][CH2:39][CH2:38][N:37]3[CH2:41][CH3:42])=[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

5

반응물 3

HCID 682631,1'-CarbonyldiimidazoleHCID 143904542-(3-Chlorophenyl)-3H-imidazo[4,5-b]pyridine-3-acetic acidHCID 144473471-Ethyl-2-pyrrolidineethanamine

생성물 1

HCID 143902512-(3-Chlorophenyl)-N-(1-ethyl-2-pyrrolidinylmethyl)-3H-imidazo [4,5-b]pyridine-3-acetamide hydrochloride수율 31.8%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

A solution of 2-(3-chlorophenyl)-3H-imidazo[4,5-b]pyridine-3-acetic acid (5.76 g, 0.020 mole), 1,1'-carbonyldiimidazole (3.24 g, 0.020 mole), and anhydrous tetrahydrofuran (250 ml) was stirred at room temperature with a stream of nitrogen bubbling through for 2 hrs. The nitrogen flow was stopped and a solution of 2-(aminoethyl)-1-ethyl pyrrolidine (2.56 g, 0.02 mole) in dry tetrahydrofuran (50 ml) was added. The solution was stoppered and stirred at room temperature over the weekend. The reaction was concentrated in vacuo and partitioned between ethyl acetate (100 ml) and 5% potassium hydroxide solution (50 ml). The layers were separated and the aqueous portion washed with ethyl acetate (50 ml), water (25 ml), brine (25 ml), dried over sodium sulfate, and concentrated in vacuo. The solid residue was converted to the dihydrochloride salt and crystallized from isopropyl alcohol-diethyl ether. Recrystallization from isopropyl alcohol-isopropyl ether gave 1.38 g (15%) of an off-white solid, mp 186°-190° C. with decomposition.

후처리

  1. concentrationThe reaction was concentrated in vacuo
  2. custompartitioned between ethyl acetate (100 ml) and 5% potassium hydroxide solution (50 ml)
  3. customThe layers were separated
  4. washthe aqueous portion washed with ethyl acetate (50 ml), water (25 ml), brine (25 ml)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customcrystallized from isopropyl alcohol-diethyl ether
  8. customRecrystallization from isopropyl alcohol-isopropyl ether

출처 및 근거

ORD 기록
ord-c3a9457de393402ead35da30b33d42a2
출처 데이터셋
uspto-grants-1988_09
특허 번호
US04772600

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