Potassium Carbonate → HCID 23442300, compound

HRID 2119663Notes

Reaction equation

HRID 2119663 reaction equation
[CH2:1]([N:3]1[C:12]2[CH:11]=[CH:10][C:9]([CH3:13])=[CH:8][C:7]=2[C:6](=[O:14])[C:5]2[N:15]([CH3:18])[N:16]=[CH:17][C:4]1=2)[CH3:2].CS(OC1C[CH2:28][N:27](C(OC(C)(C)C)=O)[CH2:26][CH2:25]1)(=O)=O.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH3:18][N:15]1[C:5]2[C:6](=[O:14])[C:7]3[CH:8]=[C:9]([CH3:13])[CH:10]=[CH:11][C:12]=3[N:3]([CH:1]3[CH2:25][CH2:26][NH:27][CH2:28][CH2:2]3)[C:4]=2[CH:17]=[N:16]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 41848691-(tert-Butoxycarbonyl)-4-(methanesulfonyloxy)piperidineHCID 23442433HCID 23442433, compound

Product 1

HCID 23442300HCID 23442300, compoundYield 35.2%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 21584019Toluene ethylacetateSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 1,7-dimethyl-1,4-dihydro-9H-pyrazolo[4,3-b]quinolin-9-one (EXAMPLE 47, step 2, 0.1 g, 0.47 mmol), tert-butyl 4-[(methylsulfonyl)oxy]-1-piperidinecarboxylate ((Leeson et al., Bioorg. Med. Chem. Lett., 1999, 9, 1285), 0.66 g, 2.4 mmol) and potassium carbonate (0.13 g, 0.94 mmol) in dimethylsulfoxide (15 ml) was heated at 85° C. for 46.5 h. The reaction mixture was diluted with toluene/ethyl acetate (1:3, 30 ml), washed with water (30 ml), and dried over sodium sulfate. Removal of solvent gave a residue, which was chromatographed on a column of silica gel eluting with ethyl acetate/hexane (1:1) to afford 49 mg (26%) of the title compound as a pale brown solid.

Workup

  1. washwashed with water (30 ml)
  2. dry with materialdried over sodium sulfate
  3. customRemoval of solvent
  4. customgave a residue, which
  5. customwas chromatographed on a column of silica gel eluting with ethyl acetate/hexane (1:1)

Sources & evidence

ORD record
ord-18b8c874a8f64c59b59e0a13c7b07bdd
Source dataset
uspto-grants-2004_02
Patent number
US06686373B2

Reaction notes

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