Diisopropylethylamine → HCID 178461513, compound
Reaction equation
[Cl:1][C:2]1[C:7]2[NH:8][C:9]([N:11]3[CH2:16][CH2:15][NH:14][C@H:13]([CH3:17])[CH2:12]3)=[N:10][C:6]=2[CH:5]=[C:4]([C:18]([F:21])([F:20])[F:19])[CH:3]=1.Cl[C:23]1[C:28]([C:29]([F:32])([F:31])[F:30])=[CH:27][CH:26]=[CH:25][N:24]=1.C(N(CC)C(C)C)(C)C>O>[Cl:1][C:2]1[C:7]2[NH:8][C:9]([N:11]3[CH2:16][CH2:15][N:14]([C:23]4[C:28]([C:29]([F:32])([F:31])[F:30])=[CH:27][CH:26]=[CH:25][N:24]=4)[C@H:13]([CH3:17])[CH2:12]3)=[N:10][C:6]=2[CH:5]=[C:4]([C:18]([F:21])([F:20])[F:19])[CH:3]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 250 °C
Procedure
A mixture of the piperazine from step (a) above (80 mg, 0.25 mmol), 2-chloro-3-trifluoromethyl-pyridine (54 mg, 0.3 mmol, Aldrich) and N,N-diisopropylethylamine (0.5 mL, 2.9 mmol, Aldrich) was heated in a microwave synthesizer for 120 min at 250° C. Water (10 mL) was added and the mixture was extracted with EtOAc (2×20 mL). The combined organic phases were washed with brine (10 mL), dried over Na2SO4 and filtered. The filtrate was concentrated in vacuo and the residue was purified by silica gel chromatography, eluting with 35% EtOAc/hexane to give the title compound as a white amorphous solid. MS (ESI, pos. ion) m/z: 464 (M+1).
Workup
- extractionthe mixture was extracted with EtOAc (2×20 mL)
- washThe combined organic phases were washed with brine (10 mL)
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationThe filtrate was concentrated in vacuo
- customthe residue was purified by silica gel chromatography
- washeluting with 35% EtOAc/hexane
Sources & evidence
- ORD record
- ord-16f827db7711471dbc0a84ea11be1868
- Source dataset
- uspto-grants-2011_09
- Patent number
- US08026241B2
Reaction notes
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