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 1188140Notes

Reaction equation

HRID 1188140 reaction equation
[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]

Participants

3

Reactant 1

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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%).

Workup

  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)

Sources & evidence

ORD record
ord-ac824652416d4985834a24684c84df74
Source dataset
uspto-grants-2014_03
Patent number
US08673940B2

Reaction notes

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