Diisopropylethylamine → HCID 57576369, compound
Reaction equation
C([N:8]1[CH2:12][C@H:11]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([F:20])[CH:14]=2)[C@@H:10]([C@@H:21]([O:23][C:24]2[CH:31]=[CH:30][C:27]([C:28]#[N:29])=[CH:26][N:25]=2)[CH3:22])[CH2:9]1)C1C=CC=CC=1.ClC(OC(Cl)C)=O.CCN(C(C)C)C(C)C>C1(C)C=CC=CC=1>[Cl:19][C:16]1[CH:17]=[CH:18][C:13]([C@H:11]2[CH2:12][NH:8][CH2:9][C@@H:10]2[C@@H:21]([O:23][C:24]2[CH:31]=[CH:30][C:27]([C:28]#[N:29])=[CH:26][N:25]=2)[CH3:22])=[CH:14][C:15]=1[F:20]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
To a solution of 6-{(S)-1-[(3R,4S)-1-benzyl-4-(4-chloro-3-fluoro-phenyl)-pyrrolidin-3-yl]-ethoxy}-nicotinonitrile—100 mg (0.23 mmol) dissolved in toluene (2 mL) were added 98 mg (0.69 mmol) of 1-chloroethyl chloroformate and 89 mg (0.69 mmol) of Hunig's base. The reaction mixture was heated at 100° C. for one hour. After cooling down to RT, volatiles were removed under vacuo and the crude was dissolved in MeOH (10 mL). The reaction mixture was heated at 85° C. for 30 minutes and after cooling down to RT, volatiles were removed under vacuo and the residue was directly purified on column chromatography (SiO2, CH2Cl2/MeOH 9:1) yielded 60 mg (76%) of the title compound as a light yellow oil. ES-MS m/e: 346.1 (M+H+).
Workup
- temperatureAfter cooling down to RT
- customvolatiles were removed under vacuo
- dissolutionthe crude was dissolved in MeOH (10 mL)
- temperatureThe reaction mixture was heated at 85° C. for 30 minutes
- temperatureafter cooling down to RT
- customvolatiles were removed under vacuo
- customthe residue was directly purified on column chromatography (SiO2, CH2Cl2/MeOH 9:1)
Sources & evidence
- ORD record
- ord-1f42cb6009a145dda3dd0c3fbece67f3
- Source dataset
- uspto-grants-2011_09
- Patent number
- US08012998B2
Reaction notes
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