1,2-Dichloroethane → HCID 178445100, compound

Temperature

0 °C

At 0° C., EDC (0.45 g, 2.4 mmol) was added to a solution of tert-butylacetic acid (0.30 mL, 2.3 mmol), and 1-hydroxy-7-azabenzotriazole (0.32 g, 2.4 mmol) in dichloromethane (30 mL). The reaction mixture was stirred for 20 min at 0° C. 4,5,6,7-tetrahydroimidazo[4,5-c]pyridine dihydrochloride (0.50 g, 2.4 mmol) was added. Ethyldiisopropylamine (0.40 mL, 2.4 mmol) was added. The reaction mixture was stirred for 16 h at room temperature. The reaction mixture was diluted with ethyl acetate (100 mL) and washed with 10% aqueous sodium hydrogen sulfate solution (100 mL). A 1 N solution of sodium hydroxide was added to the aqueous solution until pH 12 was obtained. It was extracted with ethyl acetate (2×100 mL). These organic extracts were dried over magnesium sulfate. The solvent was removed in vacuo. The crude product was purified by flash chromatography on silica (40 g), using dichloromethane/methanol/25% aqueous ammonia (100:10:1) as eluent to give 125 mg of the title compound.

1. stirringThe reaction mixture was stirred for 16 h at room temperature
2. washwashed with 10% aqueous sodium hydrogen sulfate solution (100 mL)
3. additionA 1 N solution of sodium hydroxide was added to the aqueous solution until pH 12
4. customwas obtained
5. extractionIt was extracted with ethyl acetate (2×100 mL)
6. dry with materialThese organic extracts were dried over magnesium sulfate
7. customThe solvent was removed in vacuo
8. customThe crude product was purified by flash chromatography on silica (40 g)

ORD record

ord-86c1139db71042f190cffc862b19a688

Source dataset

uspto-grants-2005_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06908926B1