P-Phenylenediamine → N1-(2-(1-Methyl-1H-imidazol-2-yl)thieno[3,2-b]pyridin-7-yl)benzene-1,4-diamine

HRID 1261361Notes

Reaction equation

HRID 1261361 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]3[N:12]([CH3:16])[CH:13]=[CH:14][N:15]=3)[S:10][C:3]=12.[C:17]1([NH2:24])[CH:22]=[CH:21][C:20]([NH2:23])=[CH:19][CH:18]=1>C(O)(C)C>[CH3:16][N:12]1[CH:13]=[CH:14][N:15]=[C:11]1[C:9]1[S:10][C:3]2[C:4](=[N:5][CH:6]=[CH:7][C:2]=2[NH:23][C:20]2[CH:21]=[CH:22][C:17]([NH2:24])=[CH:18][CH:19]=2)[CH:8]=1

Participants

4

Reactant 2

HCID 7814P-PhenylenediamineHCID 221435637-chloro-2-(1-methyl-1H-imidazol-2-yl)-thieno[3,2-b]pyridine

Product 1

HCID 59424632N1-(2-(1-Methyl-1H-imidazol-2-yl)thieno[3,2-b]pyridin-7-yl)benzene-1,4-diamineYield 46.7%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 214 (500 mg, 2.0 mmol, scheme 46) and benzene-1,4-diamine (500 mg, 4.62 mmol) in iso-PrOH (15 mL) was refluxed overnight, cooled to room temperature and filtered. The solid was collected, washed with iso-PrOH/H2O mixture, to afford the title compound 301 (300 mg, 44% yield) as a yellowish solid. MS (m/z): 322.1(M+H) (found).

Workup

  1. temperaturewas refluxed overnight
  2. filtrationfiltered
  3. customThe solid was collected
  4. washwashed with iso-PrOH/H2O mixture

Sources & evidence

ORD record
ord-0f5d6a478174482996cc0a7b70e209f7
Source dataset
uspto-grants-2013_06
Patent number
US08470850B2

Reaction notes

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