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3-Amino-1-propanol → 5-[2-[3-(Hydroxy)propylcarbamoyloxy]ethylthio]imdazo[1,2-a]pyridine

HRID 5447
Notes
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Reaction equation

HRID 5447 reaction equation
O([C:8]([O:10][CH2:11][CH2:12][S:13][C:14]1[N:19]2[CH:20]=[CH:21][N:22]=[C:18]2[CH:17]=[CH:16][CH:15]=1)=[O:9])C1C=CC=CC=1.[NH2:23][CH2:24][CH2:25][CH2:26][OH:27]>C(Cl)(Cl)Cl>[OH:27][CH2:26][CH2:25][CH2:24][NH:23][C:8]([O:10][CH2:11][CH2:12][S:13][C:14]1[N:19]2[CH:20]=[CH:21][N:22]=[C:18]2[CH:17]=[CH:16][CH:15]=1)=[O:9]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 90863-Amino-1-propanolHCID 233628305-[2-(Phenoxycarbonyloxy)ethylthio]imidazo[1,2-a]pyridine

Product 1

HCID 233628315-[2-[3-(Hydroxy)propylcarbamoyloxy]ethylthio]imdazo[1,2-a]pyridineYield 55.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
120 °C

Procedure

To 5-[2-(phenoxycarbonyloxy)ethylthio]imidazo[1,2-a]pyridine (1.10 g, 3.50 mmoles) was added 3-aminopropanol (0.27 ml, 3.52 mmoles) and the mixture was stirred at 120° C. for 1.5 hours. The reaction mixture was cooled by standing and chloroform was added thereto, which was washed with water and dried over anhydrous magnesium sulfate, and then the solvent was distilled off. Then, the residue was purified by column chromatography (eluent: methanol/chloroform=1:20) to obtain 575 mg of the desired product (55.6%, colorless crystals).

Workup

  1. temperatureThe reaction mixture was cooled
  2. washwhich was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off
  5. customThen, the residue was purified by column chromatography (eluent: methanol/chloroform=1:20)

Sources & evidence

ORD record
ord-349268ab472d46378b63207ed9f22d8d
Source dataset
uspto-grants-1993_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05244908

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes