Cesium carbonate → HCID 70048870, compound

HRID 864756Notes

Reaction equation

HRID 864756 reaction equation
Cl.[Cl:2][C:3]1[C:4]([O:13][CH2:14][CH2:15][N:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)=[N:5][CH:6]=[C:7]([Cl:12])[C:8]=1[C:9]([OH:11])=[O:10].C(=O)([O-])[O-].[Cs+].[Cs+].Cl[CH2:29][N:30]1[C:40](=[O:41])[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][C:38]=2[CH:42]([CH3:44])[CH3:43])[S:31]1(=[O:33])=[O:32]>CO>[ClH:2].[Cl:2][C:3]1[C:4]([O:13][CH2:14][CH2:15][N:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)=[N:5][CH:6]=[C:7]([Cl:12])[C:8]=1[C:9]([O:11][CH2:29][N:30]1[C:40](=[O:41])[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][C:38]=2[CH:42]([CH3:44])[CH3:43])[S:31]1(=[O:32])=[O:33])=[O:10]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 10446001HCID 10446001, compoundHCID 70048242HCID 70048242, compound

Product 1

HCID 70048870HCID 70048870, compoundYield 16.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

A solution of the free base of 3,5-dichloro-2-[2-(4-morpholinyl) ethoxy) pyridine-4-carboxylic acid hydrochloride (3.6 g, 0.01 mol) and cesium carbonate (4.85 g, 0.015 mol) in methanol (50 ml) was stirred for 30 minutes. The methanol was removed in vacuo and the residue was dissolved in DMF (50 ml). 2-Chloromethyl-4-(isopropyl)saccharin (3.0 g, 0.01 mol) was then added and the reaction mixture was heated at 80° C. for 3 hours. The DMF was removed in vacuo, the residue was taken up in methylene chloride and was filtered through charcoal. The solvent was removed in vacuo, the residue was taken up in tert-butyl-methylether and the solution was filtered. The solvent was removed in vacuo and the residue was treated with ethereal HCl. A gum was obtained which was triturated with CH3CN to afford 0.5 g (9%) of 4-(isopropyl]-2-saccharinylmethyl 3.5-dichloro-2-[2-(4-morpholinyl)ethoxy]pyridine-4-carboxylate hydrochloride as a white solid, m.p. 120°-140° C.

Workup

  1. customThe methanol was removed in vacuo
  2. dissolutionthe residue was dissolved in DMF (50 ml)
  3. customThe DMF was removed in vacuo
  4. filtrationwas filtered through charcoal
  5. customThe solvent was removed in vacuo
  6. filtrationthe solution was filtered
  7. customThe solvent was removed in vacuo
  8. additionthe residue was treated with ethereal HCl
  9. customA gum was obtained which
  10. customwas triturated with CH3CN

Sources & evidence

ORD record
ord-c9e8dad0f01547d4b720a6cfce8eec14
Source dataset
uspto-grants-1996_10
Patent number
US05563163

Reaction notes

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