Hydrochloric Acid → HCID 19377398, compound

HRID 2210748Notes

Reaction equation

HRID 2210748 reaction equation
[C:1]([O:4][CH:5]([C:8]1[C:9]([S:14]([NH2:17])(=[O:16])=[O:15])=[N:10][CH:11]=[CH:12][CH:13]=1)[CH2:6][F:7])(=[O:3])[CH3:2].C1([O:24][C:25](=O)[NH:26][C:27]2[N:32]=[C:31]([O:33][CH3:34])[CH:30]=[C:29]([O:35][CH3:36])[N:28]=2)C=CC=CC=1.N12CCCN=C1CCCCC2.Cl>C(#N)C.CCOCC>[C:1]([O:4][CH:5]([C:8]1[C:9]([S:14]([NH:17][C:25]([NH:26][C:27]2[N:28]=[C:29]([O:35][CH3:36])[CH:30]=[C:31]([O:33][CH3:34])[N:32]=2)=[O:24])(=[O:15])=[O:16])=[N:10][CH:11]=[CH:12][CH:13]=1)[CH2:6][F:7])(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 10945667Carbamic acid, N-(4,6-dimethoxy-2-pyrimidinyl)-, phenyl esterHCID 193774133-[1-(Acetyloxy)-2-fluoroethyl]-2-pyridinesulfonamide

Product 1

HCID 19377398HCID 19377398, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Procedure

To 4.1 g of 3-(1-acetoxy-2-fluoroethyl)-2-pyridinesulfonamide in 50 ml of acetonitrile is added 4.22 g of phenyl(4,6-dimethoxypyrimidin-2-yl)carbamate and 2.4 g of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU). After stirring at room temperature for 2 hours the solution is acidified to pH 4.5 with 5% hydrochloric acid. The resultant solution is extracted with methylene chloride and the methylene chloride phase is dried over magnesium sulfate, filtered and evaporated. Trituration of the residue with Et2O yields 6 g of the product (solid, Yield: 89%), which is washed with a mixture solvent of ethylacetate/n-hexane(1/1).

Workup

  1. extractionThe resultant solution is extracted with methylene chloride
  2. dry with materialthe methylene chloride phase is dried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-90a921a63a7d48ba8c5ebcdbe5c5d637
Source dataset
uspto-grants-1995_10
Patent number
US05461026

Reaction notes

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