1,2-Dichloroethane → HCID 11151333, compound
Reaction equation
[CH2:1](Cl)[CH2:2]Cl.[CH:5]1[CH:6]=[CH:7][C:8]2N(O)N=N[C:9]=2[CH:10]=1.[CH3:15][N:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1.ClCCl.[CH3:25][OH:26].[CH3:27][N:28]([CH3:31])C=O>>[CH3:15][N:16]1[CH2:21][CH2:20][N:19]([C:25]([C:10]2[C:9]([C:8]3[C:1]4[C:2](=[CH:6][CH:5]=[CH:10][CH:9]=4)[CH:5]=[CH:6][CH:7]=3)=[CH:27][NH:28][CH:31]=2)=[O:26])[CH2:18][CH2:17]1Participants
Conditions
- Temperature
- 0 °C
Procedure
234 mg(1 mmol) of the compound prepared in Preparation 2-3) was dissolved in 2 ml of dimethylformamide, 230 mg(1.2 mmol) of EDC and 162 mg(1.7 mmol) of HOBT were added thereto, and the resulting mixture was stirred for 5 minutes at 0° C. To this reaction solution was added 88 mg(1 mmol) of N-methylpiperazine, which was then stirred for 5 hours at room temperature. The solvent was removed under reduced pressure and 10 ml of saturated aqueous potassium carbonate solution was added to the residue. The resulting mixture was extracted with ethyl acetate, washed with aqueous sodium chloride solution and water and then concentrated. The concentrate was subjected to silica gel column chromatography(eluent: dichloromethane/methanol=85/15, v/v) to obtain 240 mg(0.75 mmol) of the title compound.
Workup
- stirringwas then stirred for 5 hours at room temperature
- customThe solvent was removed under reduced pressure and 10 ml of saturated aqueous potassium carbonate solution
- additionwas added to the residue
- extractionThe resulting mixture was extracted with ethyl acetate
- washwashed with aqueous sodium chloride solution and water
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-5218979c66ff45df8616f639e1233098
- Source dataset
- uspto-grants-2002_08
- Patent number
- US06436960B1
Reaction notes
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