Trichloroisocyanuric Acid → 4-[(2-isopropoxyethyl)amino]-1H-imidazole-5-carboxamide

Temperature

0 °C

Trichlorocyanuric acid (1.23 g, 5.29 mmol) was added to a solution of 2-isopropoxyethanol (0.50 g, 4.80 mmol) in CH2Cl2 (3 mL). The reaction mixture was cooled to 0° C. and TEMPO (0.015 g, 0.09 mmol) was carefully added in small portions. The mixture was stirred at r.t. for 20 minutes and then filtrated through Celite and washed with CH2Cl2. The filtrate was kept cold, 0° C., during the filtration. The obtained aldehyde solution was added to a stirred mixture of 4-amino-1H-imidazole-5-carboxamide hydrochloride (0.78 g, 4.80 mmol), which was obtained from Example 3(b), at 0° C. in MeOH (5 mL). The mixture was stirred for 20 minutes, then NaCNBH4 (0.30 g, 4.80 mmol) was added. After stirring at r.t for 5 h the mixture was concentrated and purified by flash chromatography (CH2Cl2/methanol gradient; 0 to 5% methanol), to yield the title compound (0.39 g, 38%) as an oil.

1. filtrationfiltrated through Celite
2. washwashed with CH2Cl2
3. filtrationThe filtrate was kept cold, 0° C., during the filtration
4. stirringThe mixture was stirred for 20 minutes
5. additionNaCNBH4 (0.30 g, 4.80 mmol) was added
6. stirringAfter stirring at r.t for 5 h the mixture
7. concentrationwas concentrated
8. custompurified by flash chromatography (CH2Cl2/methanol gradient; 0 to 5% methanol)

ORD record

ord-6673139033054c94a3ee28934054b163

Source dataset

uspto-grants-2011_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07943625B2