Dipropylamine → HCID 58298340, compound

HRID 425247Notes

Reaction equation

HRID 425247 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([C:9]2[CH:10]=[C:11]([C:22]([NH2:24])=[O:23])[N:12]3[C:17](S(C)=O)=[CH:16][C:15]([CH3:21])=[N:14][C:13]=23)=[C:4]([CH3:25])[CH:3]=1.[CH2:26]([NH:29][CH2:30][CH2:31][CH3:32])[CH2:27][CH3:28].C(=O)([O-])O.[Na+]>C(O)C>[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([C:9]2[CH:10]=[C:11]([C:22]([NH2:24])=[O:23])[N:12]3[C:17]([N:29]([CH2:30][CH2:31][CH3:32])[CH2:26][CH2:27][CH3:28])=[CH:16][C:15]([CH3:21])=[N:14][C:13]=23)=[C:4]([CH3:25])[CH:3]=1

Participants

5

Reactant 3

HCID 8902DipropylamineHCID 516892Sodium BicarbonateHCID 58298341HCID 58298341, compound

Product 1

HCID 58298340HCID 58298340, compoundYield 45.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 8-(4-bromo-2,6-dimethyl-phenyl)-4-methanesulfinyl-2-methyl-pyrrolo[1,2-a]pyrimidine-6-carboxylic acid amide (100 mg), N,N-dipropylamine (48 mg) in ethanol (1 mL) was heated at reflux for 1 h. The reaction mixture was cooled to room temperature, poured into a saturated aqueous sodium hydrogencarbonate, and then extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure and the residue was purified by a silica gel column chromatography (silica gel: Wako Gel (C200), eluent: hexane/ethyl acetate=1:1) to give a solid. The solid was washed with a mixture of diisopropylether and ethyl acetate to give the title compound (50 mg).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1 h
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. customthe residue was purified by a silica gel column chromatography (silica gel: Wako Gel (C200), eluent: hexane/ethyl acetate=1:1)
  9. customto give a solid
  10. washThe solid was washed with a mixture of diisopropylether and ethyl acetate

Sources & evidence

ORD record
ord-be8c9391d91649c1a50b0b9699975e0a
Source dataset
uspto-grants-2012_01
Patent number
US08106194B2

Reaction notes

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