HCID 59408775, compound → HCID 25000776, compound

HRID 1188106Notes

Reaction equation

HRID 1188106 reaction equation
[CH2:1]([NH:8][C:9]1[S:10][C:11]([C:14]([NH:16][C:17]2[S:18][C:19]([C:22]3[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=3)=[CH:20][N:21]=2)=O)=[CH:12][N:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C1COCC1>[CH2:1]([NH:8][C:9]1[S:10][C:11]([CH2:14][NH:16][C:17]2[S:18][C:19]([C:22]3[CH:23]=[CH:24][C:25]([CH3:28])=[CH:26][CH:27]=3)=[CH:20][N:21]=2)=[CH:12][N:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 59408775HCID 59408775, compound

Product 1

HCID 25000776HCID 25000776, compoundYield 18.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

BMS (0.2 mL, 2.1 mmol) was added to a solution of 2-(benzylamino)-N-(5-p-tolylthiazol-2-yl)thiazole-5-carboxamide (170 mg, 0.42 mmol) in THF (6 mL) at RT. The resulting solution was stirred at reflux overnight. The reaction was then quenched with MeOH (2 mL) and 1N HCl was added until the pH reached 2. After stirring the reaction mixture at reflux temperature for 12 hrs, the organic solvents were evaporated and the aqueous solution was neutralized with 1N NaOH, extracted with CHCl3, dried with Na2SO4 and concentrated. The crude product was purified by column (AcOEt), yielding N-benzyl-5-((5-p-tolylthiazol-2-ylamino)methyl)thiazol-2-amine (30 mg, 18%).

Workup

  1. temperatureat reflux overnight
  2. customThe reaction was then quenched with MeOH (2 mL) and 1N HCl
  3. additionwas added until the pH
  4. stirringAfter stirring the reaction mixture
  5. temperatureat reflux temperature for 12 hrs
  6. customthe organic solvents were evaporated
  7. extractionextracted with CHCl3
  8. dry with materialdried with Na2SO4
  9. concentrationconcentrated
  10. customThe crude product was purified by column (AcOEt)

Sources & evidence

ORD record
ord-1f32a05b3d224cd097b1b6dff496d82c
Source dataset
uspto-grants-2014_03
Patent number
US08673940B2

Reaction notes

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