Formic Acid → HCID 10004184, compound
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]([CH2:22][C@H:23]2[CH2:28][CH2:27][CH2:26][S:25][CH2:24]2)[C:13]([NH:15][C:16]2[CH:21]=[N:20][CH:19]=[CH:18][N:17]=2)=[O:14])[CH:5]=[CH:6][C:7]=1[S:8]([CH3:11])(=[O:10])=[O:9].C(O)=[O:30].OO>>[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]([CH2:22][C@H:23]2[CH2:28][CH2:27][CH2:26][S:25](=[O:30])[CH2:24]2)[C:13]([NH:15][C:16]2[CH:21]=[N:20][CH:19]=[CH:18][N:17]=2)=[O:14])[CH:5]=[CH:6][C:7]=1[S:8]([CH3:11])(=[O:10])=[O:9]Participants
Conditions
- Temperature
- 0 °C
Procedure
A slurry of 2-(3-chloro-4-methanesulfonyl-phenyl)-N-pyrazin-2-yl-3-(tetrahydro-thiopyran-3(R)-yl)-propionamide (prepared as in Example 18, 10.0 mg, 0.0227 mmol) in formic acid (68.5 μL, 1.816 mmol) cooled to 0° C. was treated with a 30% aqueous hydrogen peroxide solution (7.7 μL, 0.068). The resulting solution was stirred at 0° C. for 10 min. The reaction was quenched by the addition of a 10% aqueous sodium sulfite solution (1 mL) and then extracted with ethyl acetate (2×5 mL). The organics were dried over magnesium sulfate, filtered, and concentrated in vacuo. Biotage chromatography (FLASH 12S, Silica, 93/7 chloroform/methanol) afforded 2-(3-chloro-4-methanesulfonyl-phenyl)-3-(1-oxo-hexahydro-1λ4-thiopyran-3(R)-yl)-N-pyrazin-2-yl-propionamide (10.0 mg, 96.5%) as a beige gum: EI-HRMS m/e calcd for C19H22ClN3O4S2 (M+Na)+ 478.0632. found 478.0632.
Workup
- customThe reaction was quenched by the addition of a 10% aqueous sodium sulfite solution (1 mL)
- extractionextracted with ethyl acetate (2×5 mL)
- dry with materialThe organics were dried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-159d624b3cb64406be26fa79b071ffd2
- Source dataset
- uspto-grants-2007_08
- Patent number
- US07259166B2
Reaction notes
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