Potassium Carbonate → HCID 58932629, compound
Reaction equation
[CH:1]1([CH2:6][C@H:7]([OH:28])[CH2:8]OS(C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)(=O)=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl:29][C:30]1[C:38]([Cl:39])=[CH:37][C:33]2[N:34]=[CH:35][NH:36][C:32]=2[CH:31]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH:1]1([CH2:6][C@H:7]([OH:28])[CH2:8][N:34]2[C:33]3[CH:37]=[C:38]([Cl:39])[C:30]([Cl:29])=[CH:31][C:32]=3[N:36]=[CH:35]2)[CH2:2][CH2:3][CH2:4][CH2:5]1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 160 °C
Procedure
Two large (2-5 mL) microwave reactor tubes were charged with (S)-2,4,6-Triisopropyl-benzenesulfonic acid 3-cyclopentyl-2-hydroxy-propyl ester (Example 6, Step A, 1.88 g, 4.6 mmol), 5,6-dichlorobenzimidazole (859 mg, 4.6 mmol), K2CO3 (1.27 g, 9.2 mmol) and DMF (4 mL). The tubes were then heated to 160° C. for 6 minutes. The reaction was partitioned between ethyl acetate and water. The aqueous layer was extracted a total of 2 times with ethyl acetate and the combined organics were dried over MgSO4. The solvent was removed and the resulting oil was chromatographed over silica gel using a linear gradient of 0-100% ethyl acetate in hexane to afford 566 mg (40%) of the title compound as a solid: HPLC-MS calcd. for C15H18Cl2N2O (M+H+) 313.1, found 313.2.
Workup
- customThe reaction was partitioned between ethyl acetate and water
- extractionThe aqueous layer was extracted a total of 2 times with ethyl acetate
- dry with materialthe combined organics were dried over MgSO4
- customThe solvent was removed
- customthe resulting oil was chromatographed over silica gel using a linear gradient of 0-100% ethyl acetate in hexane
Sources & evidence
- ORD record
- ord-04f148b6dc834707877bee4335ee65b4
- Source dataset
- uspto-grants-2009_03
- Patent number
- US07507755B2
Reaction notes
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