Hydrochloric Acid → N-[6-(3-hydroxypropyloxy)-5-(2-methoxyphenoxy)-2-(2-pyrimidinyl)-4-pyrimidinyl]-2-phenylethenesulfonamide

HRID 2287366Notes

Reaction equation

HRID 2287366 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.[CH2:37]([OH:41])[CH2:38][CH2:39][OH:40]>>[OH:40][CH2:39][CH2:38][CH2:37][O:41][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]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 104421,3-PropanediolHCID 5360545SodiumHCID 53744388N-[6-chloro-5-(2-methoxyphenoxy)-2-(2-pyrimidinyl)-4-pyrimidinyl]-2-phenylethenesulfonamide

Product 1

HCID 54390431N-[6-(3-hydroxypropyloxy)-5-(2-methoxyphenoxy)-2-(2-pyrimidinyl)-4-pyrimidinyl]-2-phenylethenesulfonamideYield 80.5%

Procedure

Sodium (1.031 g) was dissolved in 20.130 g of 1,3-propanediol and 2.091 g 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 room temperature for 50 minutes and then at 60° C. for 50 minutes 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 20:1). The resulting syrup was crystallized in ether and collected by filtration to give 1.817 g of N-[6-(3-hydroxypropyloxy)-5-(2-methoxyphenoxy)-2-(2-pyrimidinyl)-4-pyrimidinyl]-2-phenylethenesulfonamide.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 50 minutes
  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 20:1)
  7. customThe resulting syrup was crystallized in ether
  8. filtrationcollected by filtration

Sources & evidence

ORD record
ord-2a6934b7b995466bbdc699a7ef7db763
Source dataset
uspto-grants-2000_07
Patent number
US06083955

Reaction notes

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