Sulfuric Acid → (4-Chloro-phenyl)-{5-[2-(4,5-dihydro-1H-imidazol-2-yl)pyridin-4-yloxy]-1-methyl-1H-benzoimidazol-2-yl}-amine

HRID 2070253Notes

Reaction equation

HRID 2070253 reaction equation
OS(O)(=O)=O.[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14]2[N:18]([CH3:19])[C:17]3[CH:20]=[CH:21][C:22]([O:24][C:25]4[CH:30]=[CH:29][N:28]=[C:27]([C:31]#[N:32])[CH:26]=4)=[CH:23][C:16]=3[N:15]=2)=[CH:9][CH:8]=1.[CH2:33](N)[CH2:34][NH2:35]>>[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14]2[N:18]([CH3:19])[C:17]3[CH:20]=[CH:21][C:22]([O:24][C:25]4[CH:30]=[CH:29][N:28]=[C:27]([C:31]5[NH:35][CH2:34][CH2:33][N:32]=5)[CH:26]=4)=[CH:23][C:16]=3[N:15]=2)=[CH:9][CH:8]=1

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 3301EthylenediamineHCID 220404424-[2-(4-chlorophenylamino)-1-methyl-1H-benzoimidazol-5-yloxy]-pyridine-2-carbonitrile

Product 1

HCID 22040586(4-Chloro-phenyl)-{5-[2-(4,5-dihydro-1H-imidazol-2-yl)pyridin-4-yloxy]-1-methyl-1H-benzoimidazol-2-yl}-amine

Procedure

H2SO4 (454 mg) was added cautiously to a suspension of 4-[2-(4-chloro-phenylamino)-1-methyl-1H-benzoimidazol-5-yloxy]-pyridine-2-carbonitrile (60.0 mg) in ethylenediamine (0.50 mL). The system was shaken at room temperature for 72 hrs, then poured onto ice/NaHCO3. The solid product was collected, washed (H2O) air-dried 59.8 mg. M/z=419 (M+1).

Workup

  1. additionpoured onto ice/NaHCO3
  2. customThe solid product was collected
  3. washwashed (H2O)
  4. customair-dried 59.8 mg

Sources & evidence

ORD record
ord-92b2246f4a0d4175ad3830a4cbbcd54f
Source dataset
uspto-grants-2012_10
Patent number
US08299108B2

Reaction notes

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