Methanol → Avosentan

HRID 1059704ノート

反応式

HRID 1059704 の反応式
[Na].Cl[C:3]1[N:8]=[C:7]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=2)[N:6]=[C:5]([NH:15][S:16]([C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][N:20]=2)(=[O:18])=[O:17])[C:4]=1[O:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[O:33][CH3:34].[CH3:35][OH:36]>>[CH3:35][O:36][C:3]1[N:8]=[C:7]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=2)[N:6]=[C:5]([NH:15][S:16]([C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][N:20]=2)(=[O:18])=[O:17])[C:4]=1[O:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[O:33][CH3:34]

参加物

4

反応物 3

HCID 887MethanolHCID 5360545SodiumHCID 11202530HCID 11202530、化合物

生成物 1

HCID 9912992Avosentan

実験手順

To a solution of 6.9 g sodium in MeOH (300 ml) were added 14.52 g of 5-methyl-pyridine-2-sulfonic acid[6-chloro-5-(2-methoxy-phenoxy)-2-pyridin-4-yl-pyrimidin-4-yl]-amide at RT and the mixture was refluxed for 5 days until completion of the reaction according to TLC analysis. The reaction mixture was concentrated in vacuo to half its volume upon which the crude reaction product precipitated as a sodium salt. It was filtered off by suction and dried in a high vacuum. The solid was dissolved in water, which was then made acidic by addition of acetic acid. The precipitating free sulfonamide was extracted into Me2Cl2. The organic layer was dried over Mg2SO4, concentrated on a rotary evaporator, and the crystalline solid that had formed was filtered off. It was then dried in a high vacuum for 12 h at 120° C. to give the desired 5-methyl-pyridine-2-sulfonic acid[6-methoxy-5-(2-methoxy-phenoxy)-2-pyridin-4-yl-pyrimidin-4-yl]-amide as white crystals. Melting point 225-226° C. ISN mass spectrum, m/e 478.2 (M-1 calculated for C23H21N5O5S1: 478).

後処理

  1. temperaturethe mixture was refluxed for 5 days until completion of the reaction
  2. concentrationThe reaction mixture was concentrated in vacuo to half its volume upon which the crude
  3. customreaction product
  4. customprecipitated as a sodium salt
  5. filtrationIt was filtered off by suction
  6. customdried in a high vacuum
  7. dissolutionThe solid was dissolved in water
  8. additionmade acidic by addition of acetic acid
  9. extractionThe precipitating free sulfonamide was extracted into Me2Cl2
  10. dry with materialThe organic layer was dried over Mg2SO4
  11. concentrationconcentrated on a rotary evaporator
  12. customthe crystalline solid that had formed
  13. filtrationwas filtered off
  14. customIt was then dried in a high vacuum for 12 h at 120° C.

出典と根拠

ORDレコード
ord-bb4ac3351ff54e66b1b809269e6200b9
出典データセット
uspto-grants-2003_02
特許番号
US06521631B2

反応ノート

読み込み中…