1,2-Dichloroethane → HCID 178520154, compound
Reaction equation
C(Cl)CCl.ON1C2N=CC=CC=2N=N1.[CH:15]12[CH2:21][CH:18]([CH2:19][CH2:20]1)[CH2:17][CH:16]2[CH2:22][C:23]([OH:25])=O.[NH:26]1[C:34]2[CH2:33][CH2:32][NH:31][CH2:30][C:29]=2[N:28]=[CH:27]1.C(N(C(C)C)C(C)C)C>ClCCl.C(OCC)(=O)C>[CH:15]12[CH2:21][CH:18]([CH2:19][CH2:20]1)[CH2:17][CH:16]2[CH2:22][C:23]([N:31]1[CH2:32][CH2:33][C:34]2[NH:26][CH:27]=[N:28][C:29]=2[CH2:30]1)=[O:25]Participants
Conditions
- Temperature
- 0 °C
Procedure
At 0° C., EDC (0.45 g, 2.4 mmol) was added to a solution of 1-hydroxy-7-azabenzotriazole (0.32 g, 2.4 mmol) and 2-norbornaneacetic acid (0.338 mL, 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 dihycrochloride (0.50 g, 2.3 mmol) was added. Ethyldiisopropylamine (0.40 mL, 2.3 mmol) was added. The reaction mixture was stirred for 16 h at room temperature. It was diluted with ethyl acetate (100 mL) and washed with a saturated aqueous solution of sodium hydrogencarbonate (100 mL). The aqueous solution was extracted with ethyl acetate (2×60 mL). The combined organic layers 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 120 mg of the title compound.
Workup
- stirringThe reaction mixture was stirred for 16 h at room temperature
- washwashed with a saturated aqueous solution of sodium hydrogencarbonate (100 mL)
- extractionThe aqueous solution was extracted with ethyl acetate (2×60 mL)
- dry with materialThe combined organic layers were dried over magnesium sulfate
- customThe solvent was removed in vacuo
- customThe crude product was purified by flash chromatography on silica (40 g)
Sources & evidence
- ORD record
- ord-50b191e3cf6343b5b796b9db8350c38a
- Source dataset
- uspto-grants-2005_06
- Patent number
- US06908926B1
Reaction notes
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