4,6-Dichloro-5-(2-methoxy-phenoxy)-2-morpholin-4-yl-pyrimidine → 5-Isopropyl-pyridine-2-sulfonic acid 6-chloro-5-(2-methoxy-phenoxy)-2-morpholin-4-yl-pyrimidin-4-yl-amide

HRID 356655

反応式

HRID 356655 の反応式
Cl[C:2]1[C:7]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[O:15][CH3:16])=[C:6]([Cl:17])[N:5]=[C:4]([N:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)[N:3]=1.[K+].[CH:25]([C:28]1[CH:29]=[CH:30][C:31]([S:34]([NH-:37])(=[O:36])=[O:35])=[N:32][CH:33]=1)([CH3:27])[CH3:26]>CS(C)=O>[Cl:17][C:6]1[N:5]=[C:4]([N:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)[N:3]=[C:2]([NH:37][S:34]([C:31]2[CH:30]=[CH:29][C:28]([CH:25]([CH3:27])[CH3:26])=[CH:33][N:32]=2)(=[O:36])=[O:35])[C:7]=1[O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[O:15][CH3:16]

参加物

4

反応物 2

HCID 219795314,6-Dichloro-5-(2-methoxy-phenoxy)-2-morpholin-4-yl-pyrimidineHCID 1317209445-Isopropyl pyridine-2-sulfonamide potassium salt

生成物 1

HCID 227294065-Isopropyl-pyridine-2-sulfonic acid 6-chloro-5-(2-methoxy-phenoxy)-2-morpholin-4-yl-pyrimidin-4-yl-amide収率 96.4%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

A solution of 1.18 g of 4,6-dichloro-5-(2-methoxy-phenoxy)-2-morpholin-4-yl-pyrimidine and 2.12 g (8.88 mmol) of 5-isopropyl-pyridine-2-sulphonamide potassium salt in 25 ml of dry DMSO was heated to 80° C. for 3 hours until the dichloride had disappeared completely. The DMSO was removed in a high vacuum, the residue was taken up with 60 ml of water and the aqueous solution was washed three times with diethyl ether. The solution was then acidified to pH 3.5 with 1N HCl and the product was extracted three times with ethyl acetate. The organic phases were washed twice with water and finally once with saturated sodium chloride solution, combined, dried with sodium sulphate and evaporated. The crystalline residue was digested twice with absolute diethyl ether in order to completely remove a trace of 5-isopropyl-pyridine-2-sulphonamide. The crystals remaining behind were filtered off and dried. There were obtained 1.66 g (96%) of 5-isopropyl-pyridine-2-sulphonic acid 6-chloro-5-(2-methoxy-phenoxy)-2-morpholin-4-yl-pyrimidin-4-ylamide as white crystals of m.p. 168°-176° C., MS: (M-H)- =518.3.

後処理

  1. customThe DMSO was removed in a high vacuum
  2. washthe aqueous solution was washed three times with diethyl ether
  3. extractionthe product was extracted three times with ethyl acetate
  4. washThe organic phases were washed twice with water and finally once with saturated sodium chloride solution
  5. dry with materialdried with sodium sulphate
  6. customevaporated
  7. customto completely remove a trace of 5-isopropyl-pyridine-2-sulphonamide
  8. filtrationThe crystals remaining behind were filtered off
  9. customdried

出典と根拠

ORDレコード
ord-587d000b43c7457b8e3652f38cd3d8fa
出典データセット
uspto-grants-1998_11
特許番号
US05837708

関連ノート

読み込み中…