Potassium Carbonate → HCID 59053821, compound

HRID 2408123Notes

Reaction equation

HRID 2408123 reaction equation
[CH3:1][C:2]1([CH3:33])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([NH:14][S:15]([CH:18]3[CH2:20][CH2:19]3)(=[O:17])=[O:16])=[O:13])[CH:10]=2)[NH:5][CH:4]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([N:27]3[CH2:32][CH2:31][O:30][CH2:29][CH2:28]3)[CH:22]=2)[CH2:3]1.[C:34](=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:1][C:2]1([CH3:33])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([N:14]([CH3:34])[S:15]([CH:18]3[CH2:20][CH2:19]3)(=[O:17])=[O:16])=[O:13])[CH:10]=2)[NH:5][CH:4]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([N:27]3[CH2:28][CH2:29][O:30][CH2:31][CH2:32]3)[CH:22]=2)[CH2:3]1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 59053936HCID 59053936, compound

Product 1

HCID 59053821HCID 59053821, compoundYield 19.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

To a mixture of cyclopropanesulfonic acid [4,4-dimethyl-2-(3-morpholin-4-yl-phenyl)-1,2,3,4-tetrahydro-quinoline-6-carbonyl]-amide (100 mg, 0.21 mmol), and potassium carbonate (89.4 mg, 0.64 mmol) in N,N-dimethylformamide (4 mL) was added idomethane (0.02 mL, 0.32 mmol). The reaction mixture was stirred at 25° C. for 3 h. The reaction mixture was extracted with ethyl acetate (2×50 mL), washed with water (2×20 mL), dried over anhydrous sodium sulfate and then concentrated in vacuo. Purification by Waters automated flash system (column: Xterra 30 mm×100 mm, sample manager 2767, pump 2525, detector: ZQ mass and UV 2487, solvent system: acetonitrile and 0.1% ammonium hydroxide in water) afforded cyclopropanesulfonic acid [4,4-dimethyl-2-(3-morpholin-4-yl-phenyl)-1,2,3,4-tetrahydro-quinoline-6-carbonyl]-methyl-amide (20 mg, 19%) as a white solid: MS (ESI) M+1=484.3.

Workup

  1. additionwas added idomethane (0.02 mL, 0.32 mmol)
  2. extractionThe reaction mixture was extracted with ethyl acetate (2×50 mL)
  3. washwashed with water (2×20 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customPurification by Waters automated flash system (column: Xterra 30 mm×100 mm, sample manager 2767, pump 2525, detector: ZQ mass and UV 2487, solvent system: acetonitrile and 0.1% ammonium hydroxide in water)

Sources & evidence

ORD record
ord-b247d4fce7dc441f88deb98197a588ef
Source dataset
uspto-grants-2014_08
Patent number
US08809369B2

Reaction notes

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