Potassium Carbonate → HCID 89782949, compound

HRID 877449Notes

Reaction equation

HRID 877449 reaction equation
[CH3:1][S:2]([C:5]1[CH:6]=[C:7]([C:11]2[CH:16]=[CH:15][C:14]([C:17]3[N:21]([CH2:22][C:23]([OH:25])=[O:24])[N:20]=[C:19]([C:26]([F:29])([F:28])[F:27])[CH:18]=3)=[CH:13][CH:12]=2)[CH:8]=[CH:9][CH:10]=1)(=[O:4])=[O:3].Cl[CH2:31][S:32][CH3:33].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[CH3:1][S:2]([C:5]1[CH:6]=[C:7]([C:11]2[CH:16]=[CH:15][C:14]([C:17]3[N:21]([CH2:22][C:23]([O:25][CH2:31][S:32][CH3:33])=[O:24])[N:20]=[C:19]([C:26]([F:29])([F:27])[F:28])[CH:18]=3)=[CH:13][CH:12]=2)[CH:8]=[CH:9][CH:10]=1)(=[O:3])=[O:4]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 16916Chloromethyl methyl sulfideHCID 89782773HCID 89782773, compound

Product 1

HCID 89782949HCID 89782949, compoundYield 7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of compound 38 (0.2 g, 0.471 mmol), chloromethylmethylsulfane (0182 g, 1.89 mmol) and potassium carbonate (0.324 g, 2.36 mmol) in DMF (5 mL) was stirred at room temperature for 1 h, then heated to 100° C. for 10 h. On completion, the reaction mixture was diluted with water (30 mL) and extracted with ethyl acetate (50 mL×3). The combined organic layer was washed with saturated brine, dried over sodium sulphate and concentrated. The crude reaction mixture was purificated by prep HPLC to afford 41 (15 mg, 7%). LCMS: 485.20 (M+1)+; 1H NMR (DMSO-d6, 400 MHz) δ 8.26 (s, 1H), 8.06 (d, 1H, J=7.2 Hz), 7.99 (d, 1H, J=8 Hz), 7.93 (d, 2H, J=8.4 Hz), 7.8-7.6 (m, 3H), 6.75 (s, 1H), 5.10-5.25 (m, 2H), 3.45-3.3 (m, 2H), 3.30 (s, 3H), 1.78 (s, 3H).

Workup

  1. temperatureheated to 100° C. for 10 h
  2. extractionextracted with ethyl acetate (50 mL×3)
  3. washThe combined organic layer was washed with saturated brine
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated
  6. customThe crude reaction mixture

Sources & evidence

ORD record
ord-6a8b5b1d99dd4bdfb99e2eced128f2e6
Source dataset
uspto-grants-2015_03
Patent number
US08987318B2

Reaction notes

Loading…