Methanol → HCID 54241463, compound

HRID 2287371Notes

Reaction equation

HRID 2287371 reaction equation
S(=O)(=O)(O)O.[CH3:6][O:7][C:8]1[N:13]=[C:12]([C:14]2[N:19]=[CH:18][CH:17]=[CH:16][N:15]=2)[N:11]=[C:10]([NH:20][S:21]([CH:24]=[CH:25][C:26]2[CH:31]=[CH:30][C:29]([C:32]([OH:34])=[O:33])=[CH:28][CH:27]=2)(=[O:23])=[O:22])[C:9]=1[O:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=1[O:42][CH3:43].[CH3:44]O>>[CH3:6][O:7][C:8]1[N:13]=[C:12]([C:14]2[N:19]=[CH:18][CH:17]=[CH:16][N:15]=2)[N:11]=[C:10]([NH:20][S:21]([CH:24]=[CH:25][C:26]2[CH:27]=[CH:28][C:29]([C:32]([O:34][CH3:44])=[O:33])=[CH:30][CH:31]=2)(=[O:22])=[O:23])[C:9]=1[O:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=1[O:42][CH3:43]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 54214630HCID 54214630, compound

Product 1

HCID 54241463HCID 54241463, compound

Procedure

Concentrated sulfuric acid (0.1 ml) was added to a solution of 150 mg of N-[6-methoxy-5-(2-methoxyphenoxy)-2-(2-pyrimidinyl)-4-pyrimidinyl]-2-(4-carboxyphenyl)ethenesulfonamide in 10 ml of methanol followed by stirring overnight under a refluxing condition. The reaction mixture was concentrated in vacuo, 1N hydrochloric acid was added thereto and the mixture was extracted with ethyl acetate. The extract was washed with a saturated saline solution, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo and the resulting solid was recrystallized form ethyl acetate to give 102 mg of N-[6-methoxy-5-(2-methoxyphenoxy)-2-(2-pyrimidinyl)-4-pyrimidinyl]-2-(4-methoxycarbonylphenyl)ethenesulfon-amide.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo, 1N hydrochloric acid
  2. additionwas added
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with a saturated saline solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customthe resulting solid was recrystallized form ethyl acetate

Sources & evidence

ORD record
ord-d918262c5fea4815a8afcfc075ce17a4
Source dataset
uspto-grants-2000_07
Patent number
US06083955

Reaction notes

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