Pyridine → HCID 19978087、化合物

HRID 1449525ノート

反応式

HRID 1449525 の反応式
N1C=CC=CC=1.Cl.[CH2:8]([C:11]1[N:15]2[CH2:16][CH2:17][CH2:18][N:19]=[C:14]2[S:13][C:12]=1[C:20]([Cl:22])=[O:21])[CH2:9][CH3:10].[CH2:23]([O:25][C:26]([CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][S:33][C:34]1[CH:40]=[CH:39][C:37]([NH2:38])=[CH:36][CH:35]=1)=[O:27])[CH3:24].CN(C1C=CC=CN=1)C>CN(C)C=O>[ClH:22].[CH2:23]([O:25][C:26]([CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][S:33][C:34]1[CH:40]=[CH:39][C:37]([NH:38][C:20]([C:12]2[S:13][C:14]3=[N:19][CH2:18][CH2:17][CH2:16][N:15]3[C:11]=2[CH2:8][CH2:9][CH3:10])=[O:21])=[CH:36][CH:35]=1)=[O:27])[CH3:24]

参加物

6

反応物 4

HCID 1049PyridineHCID 218852-DimethylaminopyridineHCID 19978122HCID 19978122、化合物HCID 53640504HCID 53640504、化合物

生成物 1

HCID 19978087HCID 19978087、化合物収率 36.5%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
70 °C

実験手順

In the mixture of 50 ml of pyridine and 5 ml of dimethylformamide was suspended 0.95 g of 3-propyl-6,7-dihydro-5H-thiazolo[3,2-a]pyrimidine-2-carbonylchloride hydrochloride (described in Example 13). To the suspension was added 1.0 g of 4-(5-ethoxycarbonylpentylthio) aniline prepared in a similar manner as described in Reference Example 7 and added 43.4 mg of dimethylaminopyridine, followed by stirring at 70° C. for 16 hours. The reaction mixture was concentrated and to the concentrate was added saturated sodium hydrogencarbonate aqueous solution. The mixture was extracted with chloroform. The extract was washed with saturated sodium chloride aqueous solution and dried over anhydrous potassium carbonate. The solvent was removed under reduced pressure. The residue was dissolved in ethanol. To the mixture was added saturated hydrogenchloride diethylether solution and stirred at room temperature, following by removing the solvent under reduced pressure. The residue was purified by silica gel column chromatography (silica gel:100 g) using a mixed solvent of chloroform and methanol (10:1 by volume) as an eluent. To the resulting substance was added saturated hydrogenchloride diethylether solution. The solvent was removed under reduced pressure. The residue was recrystallized from methanol-diethylether to obtain 632 mg of the titled compound.

後処理

  1. customprepared in a similar manner
  2. concentrationThe reaction mixture was concentrated and to the concentrate
  3. additionwas added saturated sodium hydrogencarbonate aqueous solution
  4. extractionThe mixture was extracted with chloroform
  5. washThe extract was washed with saturated sodium chloride aqueous solution
  6. dry with materialdried over anhydrous potassium carbonate
  7. customThe solvent was removed under reduced pressure
  8. dissolutionThe residue was dissolved in ethanol
  9. additionTo the mixture was added saturated hydrogenchloride diethylether solution
  10. stirringstirred at room temperature
  11. customby removing the solvent under reduced pressure
  12. customThe residue was purified by silica gel column chromatography (silica gel:100 g)
  13. additionTo the resulting substance was added saturated hydrogenchloride diethylether solution
  14. customThe solvent was removed under reduced pressure
  15. customThe residue was recrystallized from methanol-diethylether

出典と根拠

ORDレコード
ord-20bfdd14740240c587dc7bc948b9d47f
出典データセット
uspto-grants-1997_02
特許番号
US05599813

反応ノート

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