Isopropyl chloroformate → 5-[4-(Isopropyloxycarbonylamino)butylthio]imidazo[1,2-a]pyridine

HRID 5486

반응식

HRID 5486 반응식
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][S:6][C:7]1[N:12]2[CH:13]=[CH:14][N:15]=[C:11]2[CH:10]=[CH:9][CH:8]=1.C(N(CC)CC)C.Cl[C:24]([O:26][CH:27]([CH3:29])[CH3:28])=[O:25]>C(Cl)Cl>[CH:27]([O:26][C:24]([NH:1][CH2:2][CH2:3][CH2:4][CH2:5][S:6][C:7]1[N:12]2[CH:13]=[CH:14][N:15]=[C:11]2[CH:10]=[CH:9][CH:8]=1)=[O:25])([CH3:29])[CH3:28]

참가 물질

5

반응물 3

HCID 7917Isopropyl chloroformateHCID 8471TriethylamineHCID 233628945-[4-(Amino)butylthio]imidazo[1,2-a]pyridine

생성물 1

HCID 233630025-[4-(Isopropyloxycarbonylamino)butylthio]imidazo[1,2-a]pyridine수율 41.9%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To 5-(4-amino)butylthioimidazo[1,2-a]pyridine (370 mg, 1.67 mmoles) and triethylamine (0.35 ml, 2.51 mmoles) in methylene chloride (20 ml) was added isopropyl chloroformate (0.25 g, 2.04 mmoles) under ice-cooling with stirring and the mixture was stirred under ice-cooling for 1 hour. The reaction mixture was washed in turn with aqueous saturated sodium bicarbonate and saturated saline, and then dried over anhydrous magnesium sulfate. After the solvent was distilled off, the residue was purified by column chromatography (eluent: ethyl acetate) to obtain 215 mg of the desired product (41.8%, light tan oily product).

후처리

  1. temperaturecooling
  2. stirringthe mixture was stirred under ice-
  3. temperaturecooling for 1 hour
  4. washThe reaction mixture was washed in turn with aqueous saturated sodium bicarbonate and saturated saline
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationAfter the solvent was distilled off
  7. customthe residue was purified by column chromatography (eluent: ethyl acetate)

출처 및 근거

ORD 기록
ord-1b45aea4222d4467b64a679104b92b1b
출처 데이터셋
uspto-grants-1993_09
특허 번호
US05244908

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