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

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]

Participants

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

temperatureThe reaction mixture was cooled
washwhich was washed with water
dry with materialdried over anhydrous magnesium sulfate
distillationthe solvent was distilled off
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

Linked notes

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