Cesium carbonate → HCID 10224583, compound

HRID 1822838Notes

Reaction equation

HRID 1822838 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:15][C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([CH2:22][OH:23])[C:17]=3[CH3:24])=[C:7]([C:12]([NH2:14])=[O:13])[CH:8]=[N:9]2)=[CH:4][C:3]=1[O:25][CH3:26].BrC[CH2:29][CH2:30][CH2:31][Cl:32].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[Cl:32][CH2:31][CH2:30][CH2:29][O:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:15][C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([CH2:22][OH:23])[C:17]=3[CH3:24])=[C:7]([C:12]([NH2:14])=[O:13])[CH:8]=[N:9]2)=[CH:4][C:3]=1[O:25][CH3:26]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 813641-Bromo-4-chlorobutaneHCID 135788286HCID 135788286, compound

Product 1

HCID 10224583HCID 10224583, compoundYield 50.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

7-Hydroxy-4-[3-(hydroxymethyl)-2-methylanilino]-6-methoxy-3-quinolinecarboxamide (0.90 mg, 2.54 mmol) was dissolved in DMF (10 ml), 1-bromo-4-chlorobutane (0.28 ml, 2.79 mmol) and Cs2CO3 (1.7 g, 5.2 mmol) were added and the mixture was stirred at ambient temperature for three days. The mixture was poured out on water and extracted with methylenechloride. The residue was chromatographed on silica using ethylacetate/methanol (1:0–>5:1) as eluent, affording 550 mg (50% yield) of the titled compound.

Workup

  1. additionThe mixture was poured out on water
  2. extractionextracted with methylenechloride
  3. customThe residue was chromatographed on silica

Sources & evidence

ORD record
ord-2775378a482f4889b241426335495bd9
Source dataset
uspto-grants-2006_05
Patent number
US07037925B2

Reaction notes

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