Hydrochloric Acid → HCID 54210385, compound

HRID 2287367Notes

Reaction equation

HRID 2287367 reaction equation
[Na].Cl[C:3]1[N:8]=[C:7]([C:9]2[N:14]=[CH:13][CH:12]=[CH:11][N:10]=2)[N:6]=[C:5]([NH:15][S:16]([CH:19]=[CH:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)(=[O:18])=[O:17])[C:4]=1[O:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[O:34][CH3:35].Cl>C(O)C#C>[CH2:28]([O:27][C:3]1[N:8]=[C:7]([C:9]2[N:14]=[CH:13][CH:12]=[CH:11][N:10]=2)[N:6]=[C:5]([NH:15][S:16]([CH:19]=[CH:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)(=[O:18])=[O:17])[C:4]=1[O:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[O:34][CH3:35])[C:29]#[CH:30]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 5360545SodiumHCID 53744388N-[6-chloro-5-(2-methoxyphenoxy)-2-(2-pyrimidinyl)-4-pyrimidinyl]-2-phenylethenesulfonamide

Product 1

HCID 54210385HCID 54210385, compoundYield 168.7%

Reagents, catalysts & solvents 1

HCID 7859Propargyl alcoholSolvent

Procedure

Sodium (185 mg) was dissolved in 5 ml of 2-propyn-1-ol and 390 mg of N-[6-chloro-5-(2-methoxyphenoxy)-2-(2-pyrimidinyl)-4-pyrimidinyl]-2-phenylethenesulfonamide was added thereto with stirring at room temperature. The reaction mixture was stirred at 60° C. for one hour and poured into a mixture of 1N hydrochloric acid and ice. This was extracted with ethyl acetate and the ethyl acetate layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated in vacuo and the resulting residue was purified by a silica gel column chromatography (chloroform-methanol=100:1 to 30:1). The resulting syrup was crystallized in ether and collected filtration to give 342 mg of N-[6-(2-propynyloxy)-5-(2-methoxyphenoxy)-2-(2-pyrimidinyl)-4-pyrimidinyl]-2-phenylethenesulfonamide.

Workup

  1. stirringThe reaction mixture was stirred at 60° C. for one hour
  2. extractionThis was extracted with ethyl acetate
  3. dry with materialthe ethyl acetate layer was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo
  6. customthe resulting residue was purified by a silica gel column chromatography (chloroform-methanol=100:1 to 30:1)
  7. customThe resulting syrup was crystallized in ether
  8. customcollected
  9. filtrationfiltration

Sources & evidence

ORD record
ord-b72f4d2a45b74de8b7192b520b7c92f7
Source dataset
uspto-grants-2000_07
Patent number
US06083955

Reaction notes

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