Hydrochloric Acid → (Z)-6,8-dihydro-8-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2-phenyl-7H-pyrrolo[2,3-g]benzothiazol-7-one
Reaction equation
[CH3:1][O:2][C:3]1[CH:7]=[CH:6][NH:5][C:4]=1[CH:8]=O.[C:10]1([C:16]2[S:17][C:18]3[C:26]([N:27]=2)=[CH:25][CH:24]=[C:23]2[C:19]=3[CH2:20][C:21](=[O:28])[NH:22]2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.N1CCCCC1.Cl>CC(O)C.O>[CH3:1][O:2][C:3]1[CH:7]=[CH:6][NH:5][C:4]=1/[CH:8]=[C:20]1\[C:21](=[O:28])[NH:22][C:23]2[CH:24]=[CH:25][C:26]3[N:27]=[C:16]([C:10]4[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=4)[S:17][C:18]=3[C:19]\1=2Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
3-Methoxypyrrole-2-carboxaldehyde (13mg, 0.105 mmol) (Bellamy, supra) and 2-phenyl-6,8-dihydro-thiazolo[5,4-e]indol-7-one (20 mg, 0.075 mmol) (from Example 5) were suspended in a solution of 10% piperidine in 2-propanol (1 mL). The mixture was heated at reflux for 3 h. The mixture was cooled, poured into water, and the aqueous mixture was made acidic with concentrated hydrochloric acid. The aqueous layer was extracted with ethyl acetate, and the combined organic extracts were washed with water, brine, and dried over anhydrous magnesium sulfate. The solvent was removed in vacuo, and the crude product was purified by reverse phase HPLC using acetonitrile—water as solvent. (Yield 10 mg, 36%).
Workup
- temperatureThe mixture was heated
- temperatureat reflux for 3 h
- temperatureThe mixture was cooled
- extractionThe aqueous layer was extracted with ethyl acetate
- washthe combined organic extracts were washed with water, brine
- dry with materialdried over anhydrous magnesium sulfate
- customThe solvent was removed in vacuo
- customthe crude product was purified by reverse phase
Sources & evidence
- ORD record
- ord-4601607ff64e41d5899a7f7ad7d96f36
- Source dataset
- uspto-grants-2001_03
- Patent number
- US06197804B1
Reaction notes
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