Ethyl Acetate → HCID 68581422, compound

HRID 2235578Notes

Reaction equation

HRID 2235578 reaction equation
Cl[C:2]1[N:6]([CH3:7])[C:5]2[C:8]([N:12]([CH:21]([CH3:23])[CH3:22])[C:13]3[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[CH:15][CH:14]=3)=[CH:9][CH:10]=[CH:11][C:4]=2[N:3]=1.[Br:24][C:25]1[CH:31]=[C:30]([CH3:32])[C:28]([NH2:29])=[CH:27][CH:26]=1.[C:33](OCC)(=[O:35])C>>[Br:24][C:25]1[CH:31]=[C:30]([CH3:32])[C:28]([NH:29][C:2]2[N:6]([CH3:7])[C:5]3[C:8]([N:12]([CH:21]([CH3:23])[CH3:22])[C:13]4[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[CH:15][CH:14]=4)=[CH:9][CH:10]=[CH:11][C:4]=3[N:3]=2)=[C:27]([O:35][CH3:33])[CH:26]=1

Participants

4

Reactant 3

HCID 8857Ethyl AcetateHCID 114234-Bromo-2-methylanilineHCID 68581136HCID 68581136, compound

Product 1

HCID 68581422HCID 68581422, compoundYield 9.5%

Conditions

Temperature
120 °C

Procedure

A mixture of 4-[(2-chloro-1-methyl-1H-benzimidazol-7-yl)(isopropyl)amino]benzonitrile (50 mg, 0.154 mmol) and 4-bromo-6-methylaniline (100 mg, 0.46 mmol) was stirred at 120° C. for 3 days. The mixture was dissolved in ethyl acetate, washed with saturated aqueous sodium bicarbonate and water, dried over magnesium sulfate and evaporated in vacuo. The residue was chromatographed on silica gel eluting with a solution of 33% ethyl acetate/hexane. The desired fractions were concentrated in vacuo, and the residual solids were washed with diethyl ether-hexane to give 7.4 mg (9.5%) of the title compound.

Workup

  1. washwashed with saturated aqueous sodium bicarbonate and water
  2. dry with materialdried over magnesium sulfate
  3. customevaporated in vacuo
  4. customThe residue was chromatographed on silica gel eluting with a solution of 33% ethyl acetate/hexane
  5. concentrationThe desired fractions were concentrated in vacuo
  6. washthe residual solids were washed with diethyl ether-hexane

Sources & evidence

ORD record
ord-26b5ee873ca847329c9a54f54cfd515e
Source dataset
uspto-grants-2010_05
Patent number
US07714009B2

Reaction notes

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