Ethyl isocyanatoacetate → HCID 11509358, compound
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([Cl:12])[CH:11]=1)[CH2:8][N:7]([CH3:13])[CH2:6][CH:5]2[C:14]1[CH:19]=[CH:18][C:17]([NH2:20])=[CH:16][CH:15]=1.[N:21]([CH2:24][C:25](OCC)=[O:26])=[C:22]=[O:23]>C(#N)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([Cl:12])[CH:11]=1)[CH2:8][N:7]([CH3:13])[CH2:6][CH:5]2[C:14]1[CH:19]=[CH:18][C:17]([N:20]2[C:25](=[O:26])[CH2:24][NH:21][C:22]2=[O:23])=[CH:16][CH:15]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
4-(6,8-Dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)phenylamine (95 mg; preparation as described in WO2004085404) was dissolved in acetonitrile (2 ml) and ethyl isocyanatoacetate (30 mg) was added dropwise with stirring. After 4 hours, the solution was concentrated and the residue purified by means of preparative HPLC. The fractions comprising product were combined, the acetonitrile was removed on a rotary evaporator, and the aqueous residue was neutralized with potassium carbonate and extracted three times with ethyl acetate. Drying over magnesium sulfate was followed by concentration to dryness. The residue was taken up with aqueous hydrochloric acid and freeze-dried. 107 mg of the desired compound were obtained.
Workup
- concentrationthe solution was concentrated
- customthe residue purified by means of preparative HPLC
- customthe acetonitrile was removed on a rotary evaporator
- extractionextracted three times with ethyl acetate
- dry with materialDrying over magnesium sulfate
- concentrationwas followed by concentration to dryness
- customfreeze-dried
Sources & evidence
- ORD record
- ord-693e392bccfa4c46934288a121fbeadc
- Source dataset
- uspto-grants-2011_01
- Patent number
- US07868003B2
Reaction notes
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