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

HRID 1670244

반응식

HRID 1670244 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 21863450Trifluoroacetic acid methylene chloride용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-34030195678644c2b21e26d6c1505759
출처 데이터셋
uspto-grants-2011_08
특허 번호
US07989477B2

연결된 노트

불러오는 중…