Hydrochloric Acid → HCID 21849968, compound
Reaction equation
[ClH:1].[C:2]([C:5]1[CH:6]=[CH:7][C:8]2[C:20]3[C:19]4[C:14]5=[C:15]([C:21](=[O:30])[N:22]([CH2:25][CH2:26][N:27]([CH3:29])[CH3:28])[C:23](=[O:24])[N:13]5[C:12]=3[CH:11]=[CH:10][C:9]=2[CH:31]=1)[CH:16]=[CH:17][CH:18]=4)(=[O:4])[CH3:3].Cl.C(=O)(O)[O-].[Na+]>C(O)(=O)C>[ClH:1].[CH3:29][N:27]([CH3:28])[CH2:26][CH2:25][N:22]1[C:21](=[O:30])[C:15]2[CH:16]=[CH:17][CH:18]=[C:19]3[C:20]4[C:8]5[CH:7]=[CH:6][C:5]([CH:2]([OH:4])[CH3:3])=[CH:31][C:9]=5[CH:10]=[CH:11][C:12]=4[N:13]([C:14]=23)[C:23]1=[O:24]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
21 μl (0.168 mmol) of a borane/pyridine complex (about 8 M) was added to a suspension of 84 mg (0.211 mmol) of a compound prepared by converting the compound of Example 2 into its free base in acetic acid (1.5 ml) and the obtained mixture was stirred at 70° C. for 3 hours. Then it was acidified by adding 1 N hydrochloric acid thereto at room temperature, stirred for 1 minute and neutralized with a saturated aqueous solution of sodium bicarbonate. Next, it was extracted by adding thereto a mixture of dichloromethane with ethanol. The organic layer was taken up, washed with water, dried over sodium sulfate and concentrated. The residue was purified by preparative thin layer chromatography and converted into its hydrochloride by using 1 N hydrochloric acid to thereby give 44 mg of the title compound.
Workup
- customprepared
- stirringat room temperature, stirred for 1 minute
- extractionNext, it was extracted
- additionby adding
- additiona mixture of dichloromethane with ethanol
- washwashed with water
- dry with materialdried over sodium sulfate
- concentrationconcentrated
- customThe residue was purified by preparative thin layer chromatography
Sources & evidence
- ORD record
- ord-ed8823fa27a144189fedbb5a1b40ff2f
- Source dataset
- uspto-grants-1999_09
- Patent number
- US05952335
Reaction notes
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