Diisopropylethylamine → HCID 178461512, compound
Reaction equation
Cl[C:2]1[NH:6][C:5]2[CH:7]=[C:8]([C:12]([F:15])([F:14])[F:13])[CH:9]=[C:10]([Cl:11])[C:4]=2[N:3]=1.[CH3:16][C@@H:17]1[CH2:22][NH:21][CH2:20][CH2:19][NH:18]1.C(N(CC)C(C)C)(C)C>CN1C(=O)CCC1.O>[Cl:11][C:10]1[C:4]2[NH:3][C:2]([N:21]3[CH2:20][CH2:19][NH:18][C@H:17]([CH3:16])[CH2:22]3)=[N:6][C:5]=2[CH:7]=[C:8]([C:12]([F:15])([F:14])[F:13])[CH:9]=1Participants
6
Conditions
- Temperature
- 120 °C
Procedure
A mixture of 2,4-dichloro-6-trifluoromethyl-1H-benzoimidazole (0.51 g, 2 mmol, Example 5b), (R)-(−)-2-methylpiperazine (0.25 g. 2.5 mmol) and N,N-diisopropylethylamine (0.5 mL, 2.9 mmol) in NMP (5 mL) was heated at 120° C. for 16 h. The reaction mixture was cooled to room temperature, diluted with water (10 mL) and 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 10% MeOH in dichloromethane to give the title compound as a light-yellow solid. MS (ESI, pos. ion) m/z: 319 (M+1).
Workup
- temperatureThe reaction mixture was cooled to room temperature
- extractionextracted 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 10% MeOH in dichloromethane
Sources & evidence
- ORD record
- ord-bb86452715214beab42c9fe07a6229f0
- Source dataset
- uspto-grants-2011_09
- Patent number
- US08026241B2
Reaction notes
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