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 1188140노트

반응식

HRID 1188140 반응식
[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]

참가 물질

3

반응물 1

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-ac824652416d4985834a24684c84df74
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08673940B2

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