Ethanethiol → HCID 178477419, compound

HRID 508582Notes

Reaction equation

HRID 508582 reaction equation
[F:1][C:2]1[CH:23]=[CH:22][C:5]2[NH:6][C:7]([CH:9]([C:11]3[CH:16]=[CH:15][C:14]([O:17][C:18]([F:21])([F:20])[F:19])=[CH:13][CH:12]=3)O)=[N:8][C:4]=2[CH:3]=1.S(Cl)(Cl)=O.[CH2:28]([SH:30])[CH3:29].CCN(C(C)C)C(C)C>C1COCC1.N1C=CC=CC=1>[CH2:28]([S:30][CH:9]([C:11]1[CH:16]=[CH:15][C:14]([O:17][C:18]([F:21])([F:20])[F:19])=[CH:13][CH:12]=1)[C:7]1[NH:6][C:5]2[CH:22]=[CH:23][C:2]([F:1])=[CH:3][C:4]=2[N:8]=1)[CH3:29]

Participants

7

Reactant 4

HCID 6343EthanethiolHCID 24386Thionyl ChlorideHCID 81531DiisopropylethylamineHCID 178519719HCID 178519719, compound

Product 1

HCID 178477419HCID 178477419, compoundYield 54.6%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8028TetrahydrofuranSolvent

Procedure

The compound of Example 1 (444 mg) was dissolved in THF (7 mL), and thionyl chloride (178 mg) and pyridine (247 mg) were added thereto. The mixture was stirred for 30 minutes at room temperature, and then ethanethiol (101 mg) and DIPEA (535 μL) were added thereto. The mixture was stirred for 1.5 hours at room temperature. After distilling off the solvent under reduced pressure, the residue was basified with a saturated aqueous solution of sodium hydrogen carbonate and extracted with chloroform. The organic layer was washed with saturated brine and then dried over anhydrous sodium sulfate. After distilling off the solvent under reduced pressure, the residue was purified by silica gel column chromatography (20% to 66% ethyl acetate/hexane), and thus the title compound (275 mg) was obtained as a colorless amorphous material.

Workup

  1. stirringThe mixture was stirred for 1.5 hours at room temperature
  2. distillationAfter distilling off the solvent under reduced pressure
  3. extractionextracted with chloroform
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationAfter distilling off the solvent under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (20% to 66% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-eb1ee1e1b6a84e0a9f50bc84af46bf18
Source dataset
uspto-grants-2015_08
Patent number
US09096531B2

Reaction notes

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