2-(propylamino)-N-(5-(4-p-tolylthiazol-2-ylcarbamoyl)thiazol-2-yl)thiazole-5-carboxamide → N-propyl-5-((5-((4-p-tolylthiazol-2-ylamino)methyl)thiazol-2-ylamino)methyl)thiazol-2-amine

HRID 1188140ノート

反応式

HRID 1188140 の反応式
[CH2:1]([NH:4][C:5]1[S:6][C:7]([C:10]([NH:12][C:13]2[S:14][C:15]([C:18](=O)[NH:19][C:20]3[S:21][CH:22]=[C:23]([C:25]4[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][CH:26]=4)[N:24]=3)=[CH:16][N:17]=2)=O)=[CH:8][N:9]=1)[CH2:2][CH3:3]>C1COCC1>[CH2:1]([NH:4][C:5]1[S:6][C:7]([CH2:10][NH:12][C:13]2[S:14][C:15]([CH2:18][NH:19][C:20]3[S:21][CH:22]=[C:23]([C:25]4[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][CH:26]=4)[N:24]=3)=[CH:16][N:17]=2)=[CH:8][N:9]=1)[CH2:2][CH3:3]

参加物

3

反応物 1

HCID 866434762-(propylamino)-N-(5-(4-p-tolylthiazol-2-ylcarbamoyl)thiazol-2-yl)thiazole-5-carboxamide

生成物 1

HCID 25001422N-propyl-5-((5-((4-p-tolylthiazol-2-ylamino)methyl)thiazol-2-ylamino)methyl)thiazol-2-amine収率 36.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

BMS (0.015 mL, 0.15 mmol) was added to a solution of 2-(propylamino)-N-(5-(4-p-tolylthiazol-2-ylcarbamoyl)thiazol-2-yl)thiazole-5-carboxamide (15 mg, 0.03 mmol) in THF (1 mL) at RT. The resulting solution was stirred at RT overnight. The reaction was then quenched with MeOH (0.5 mL). 1N HCl was added until pH=2. After stirring the reaction mixture at RT for 12 hrs, the organic solvents were evaporated and the aqueous solution was neutralized with a NaHCO3 saturated aqueous solution, extracted with AcOEt, dried with Na2SO4 and concentrated. The crude product was purified by column chromatography (0%-5% MeOH/AcOEt), yielding N-propyl-5-((5-((4-p-tolylthiazol-2-ylamino)methyl)thiazol-2-ylamino)methyl)thiazol-2-amine (5 mg, 32%).

後処理

  1. customThe reaction was then quenched with MeOH (0.5 mL)
  2. addition1N HCl was added until pH=2
  3. stirringAfter stirring the reaction mixture at RT for 12 hrs
  4. customthe organic solvents were evaporated
  5. extractionextracted with AcOEt
  6. dry with materialdried with Na2SO4
  7. concentrationconcentrated
  8. customThe crude product was purified by column chromatography (0%-5% MeOH/AcOEt)

出典と根拠

ORDレコード
ord-ac824652416d4985834a24684c84df74
出典データセット
uspto-grants-2014_03
特許番号
US08673940B2

反応ノート

読み込み中…