Potassium Carbonate → HCID 58116474, compound

HRID 661257Notes

Reaction equation

HRID 661257 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[CH:12]1[CH2:17][N:16]([C:18]([O:20]C2C=CC([N+]([O-])=O)=CC=2)=O)[CH2:15][CH:14]([C:30]([O:32][CH3:33])=[O:31])[CH2:13]1.[NH:34]1[CH2:39][CH2:38][S:37][CH2:36][CH2:35]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[F:1][C:2]1[CH:7]=[C:6]([C:8]([F:10])([F:11])[F:9])[CH:5]=[CH:4][C:3]=1[CH:12]1[CH2:17][N:16]([C:18]([N:34]2[CH2:39][CH2:38][S:37][CH2:36][CH2:35]2)=[O:20])[CH2:15][CH:14]([C:30]([O:32][CH3:33])=[O:31])[CH2:13]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 67164ThiomorpholineHCID 58116511HCID 58116511, compound

Product 1

HCID 58116474HCID 58116474, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

1.28 g (2.73 mmol) of the compound from Example 88A, 1.41 g (13.6 mmol) of thiomorpholine and 1.13 g (8.18 mmol) of potassium carbonate were added to 18 ml of DMF, and the mixture was heated in a single-mode microwave (Emrys Optimizer) at 150° C. for 40 minutes. For workup, the reaction solution was concentrated by rotary evaporation, and the residue was admixed with water. After addition of ethyl acetate and phase separation, the organic phase was washed with aqueous 1 N hydrochloric acid solution, dried (magnesium sulphate), filtered and concentrated under reduced pressure. This gave 946 mg of crude product in 72% purity (LC-MS), which was reacted without any further purification steps.

Workup

  1. concentrationFor workup, the reaction solution was concentrated by rotary evaporation
  2. additionAfter addition of ethyl acetate and phase separation
  3. washthe organic phase was washed with aqueous 1 N hydrochloric acid solution
  4. dry with materialdried (magnesium sulphate)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThis gave 946 mg of crude product in 72% purity (LC-MS), which was reacted without any further purification steps

Sources & evidence

ORD record
ord-fc81a0ec4d0449c69ba9423acb8063a7
Source dataset
uspto-grants-2011_12
Patent number
US08084469B2

Reaction notes

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