Hydrochloric Acid → HCID 54283693, compound

HRID 2287365Notes

Reaction equation

HRID 2287365 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:37](=[O:40])(O)[O-].[Na+].[NH2:42][CH:43](O)C>>[OH:40][CH2:37][CH2:43][NH:42][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

6

Reactant 5

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 522583Acetaldehyde ammoniaHCID 5360545SodiumHCID 53744388N-[6-chloro-5-(2-methoxyphenoxy)-2-(2-pyrimidinyl)-4-pyrimidinyl]-2-phenylethenesulfonamide

Product 1

HCID 54283693HCID 54283693, compound

Procedure

Sodium (693 mg) was added to and dissolved in 18.2 ml of aminoethanol. To this reaction solution was added 3.00 g of N-[6-chloro-5-(2-methoxyphenoxy)-2-(2-pyrimidinyl)-4-pyrimidinyl]-2-phenylethenesulfonamide with stirring at room temperature. The reaction mixture was stirred at 60° C. for one hour and then at 80° C. for two hours followed by pouring into a mixture of 1N hydrochloric acid and ice. This solution was neutralized with a saturated sodium bicarbonate solution and 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=20:1). The resulting amorphous substance was pulverized in ether and collected by filtration to give 2.40 g of N-[6-(2-hydroxyethylamino)-5-(2-methoxyphenoxy)-2-(2-pyrimidinyl)-4-pyrimidinyl]-2-phenylethenesulfonamide.

Workup

  1. stirringThe reaction mixture was stirred at 60° C. for one hour
  2. extractionextracted 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=20:1)
  7. filtrationcollected by filtration

Sources & evidence

ORD record
ord-2bb8aa7179674fa5ba21476e029eb2a4
Source dataset
uspto-grants-2000_07
Patent number
US06083955

Reaction notes

Loading…