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

HRID 1608602Notes

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-b4216d7723814a4caa4bdee9de07b13b
Source dataset: uspto-grants-1995_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05395839

Reaction notes

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