Imidazole → HCID 58739179, compound
Reaction equation
C(OC(=O)[NH2:7])(C)(C)C.[NH:9]1[CH:13]=[CH:12][N:11]=[CH:10]1.N1[C:27]2[C:18](=[CH:19][CH:20]=[C:21]3[C:26]=2N=CC=C3)[CH:17]=[CH:16]C=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C(OCC)(=O)C>[N:9]1([C:20]2[CH:19]=[C:18]([C@@H:17]([NH2:7])[CH3:16])[CH:27]=[CH:26][CH:21]=2)[CH:13]=[CH:12][N:11]=[CH:10]1Participants
Conditions
- Temperature
- 110 °C
Procedure
A mixture of (S)-1-(3-bromo-phenyl)-ethyl]-carbamic acid tert-butyl ester (500 mg, 1.66 mmol), imidazole (170 mg, 2.5 mmol), copper (II) triflate benzene complex (83 mg, 0.16 mmole), 1–10 phenantroline ( 300 mg, 1.66 mmole), dibenzilideneacetone (37 mg, 0.16 mmole), and cesium carbonate (595 mg, 1.86 mmole) was suspended in xylenes (1 mL) in a sealed tube. The reaction mixture was heated at 110° C. for 18 h in an oil bath and then cooled down to room temperature. Ethyl acetate (20 mL) was added, the resulting solution was washed with water (2×20 mL), and the combined organic layers were dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated in vacuo, and the crude product was dissolved in CH2Cl2 (8 mL) and trifluoroacetic acid (2 mL). The reaction mixture was stirred at room temperature for 1 h and concentrated in vacuo. The residue was purified by preparative HPLC ( NH4OAc) to give the title product (75 mg, 24% yield).
Workup
- temperaturecooled down to room temperature
- washthe resulting solution was washed with water (2×20 mL)
- dry with materialthe combined organic layers were dried over anhydrous magnesium sulfate
- filtrationfiltered
- concentrationThe filtrate was concentrated in vacuo
- dissolutionthe crude product was dissolved in CH2Cl2 (8 mL)
- concentrationconcentrated in vacuo
- customThe residue was purified by preparative HPLC ( NH4OAc)
Sources & evidence
- ORD record
- ord-4ec79b0997de416c8161afd27a7f3428
- Source dataset
- uspto-grants-2006_11
- Patent number
- US07135472B2
Reaction notes
Loading…