Cesium carbonate → HCID 9980520, compound

HRID 902040Notes

Reaction equation

HRID 902040 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([C:8]2[C:16]([C:17]3[C:26]4[C:21](=[CH:22][C:23]([OH:27])=[CH:24][CH:25]=4)[N:20]=[CH:19][CH:18]=3)=[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][N:10]3[N:9]=2)[CH:5]=[CH:4][CH:3]=1.Cl.[CH3:29][N:30]([CH3:35])[CH2:31][CH2:32][CH2:33]Cl.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[NH4+:7].[OH-:27].[CH3:29][N:30]([CH3:35])[CH2:31][CH2:32][CH2:33][O:27][C:23]1[CH:22]=[C:21]2[C:26]([C:17]([C:16]3[C:8]([C:6]4[CH:5]=[CH:4][CH:3]=[C:2]([CH3:1])[N:7]=4)=[N:9][N:10]4[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=34)=[CH:18][CH:19]=[N:20]2)=[CH:25][CH:24]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 943083-(Dimethylamino)propyl chloride hydrochlorideHCID 135983746HCID 135983746, compound

Product 2

HCID 14923Ammonium HydroxideHCID 9980520HCID 9980520, compoundYield 102.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-[2-(6-methyl-pyridin-2-yl)-pyrazolo[1,5-a]pyridin-3-yl]-quinolin-7-ol (0.1 g, 0.28 mmol) in DMF (7 mL) add 3-dimethylaminopropyl chloride hydrochloride (0.14 g, 0.86 mmol) and cesium carbonate (0.56 g, 1.71 mmol). Stir at room temperature for 48 hour. Evaporate the DMF. Add methylene chloride. Wash with water and then brine. Dry the organic layer over anhydrous Na2SO4, filter the mixture, and concentrate the mixture in vacuo. Chromatograph the residue on silica gel (elute with 100% ethyl acetate, then 1% NH4OH/5% methanol/94% methylene chloride, then 10% methanol in methylene chloride) to give the title compound 63 mg (52%) as an off-white solid.

Workup

  1. customEvaporate the DMF
  2. washWash with water
  3. dry with materialDry the organic layer over anhydrous Na2SO4
  4. filtrationfilter the mixture
  5. concentrationconcentrate the mixture in vacuo
  6. washChromatograph the residue on silica gel (elute with 100% ethyl acetate

Sources & evidence

ORD record
ord-64dc1569e4a24adaa8b33d925dde8c88
Source dataset
uspto-grants-2008_04
Patent number
US07365066B2

Reaction notes

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