P-Phenylenediamine → N1-((2-(Pyridin-2-ylamino)thiazol-5-yl)methyl)benzene-1,4-diamine

HRID 1670244Notes

Reaction equation

HRID 1670244 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8]1[S:9][C:10]([CH:13]=O)=[CH:11][N:12]=1.[C:15]1([NH2:22])[CH:20]=[CH:19][C:18]([NH2:21])=[CH:17][CH:16]=1.C([SiH](CC)CC)C>C(Cl)Cl.FC(C(O)=O)(F)F>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8]1[S:9][C:10]([CH2:13][NH:21][C:18]2[CH:19]=[CH:20][C:15]([NH2:22])=[CH:16][CH:17]=2)=[CH:11][N:12]=1

Participants

5

Reactant 3

HCID 7814P-PhenylenediamineHCID 12052TriethylsilaneHCID 220190582-(Pyridin-2-ylamino)thiazole-5-carbaldehyde

Product 1

HCID 59852979N1-((2-(Pyridin-2-ylamino)thiazol-5-yl)methyl)benzene-1,4-diamine

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

A solution of 2-(pyridine-2-ylamino)-thiazole-5-carbaldehyde (0.10 g, 0.49 mmol, WO2004/001059), benzene-1,4-diamine (0.105 g, 0.97 mmol) and triethylsilane (0.19 mL, 1.2 mmol) in CH2Cl2-TFA (3:1, 4 mL) was stirred at ambient temperature for 4 h. The reaction mixture was concentrated in vacuo and the residue partitioned between CH2Cl2 and saturated aqueous NaHCO3 solution. The organic phase was washed with saturated aqueous NaHCO3 solution, brine, dried (MgSO4) and concentrated in vacuo. The crude product which contained the title compound along with the starting aldehyde and benzene-1,4-diamine was carried on directly into the next step.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue partitioned between CH2Cl2 and saturated aqueous NaHCO3 solution
  3. washThe organic phase was washed with saturated aqueous NaHCO3 solution, brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-34030195678644c2b21e26d6c1505759
Source dataset
uspto-grants-2011_08
Patent number
US07989477B2

Reaction notes

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