N-methyl-2-pyrrolidone → N-(4-Bromo-2-methoxy-6-methylphenyl)-7-(3,5-diethyl-1H-pyrazol-1-yl)-1-methyl-1H-benzimidazol-2-amine

HRID 1698549Notes

Reaction equation

HRID 1698549 reaction equation
Cl[C:2]1[N:6]([CH3:7])[C:5]2[C:8]([N:12]3[C:16]([CH2:17][CH3:18])=[CH:15][C:14]([CH2:19][CH3:20])=[N:13]3)=[CH:9][CH:10]=[CH:11][C:4]=2[N:3]=1.[Br:21][C:22]1[CH:28]=[C:27]([CH3:29])[C:25]([NH2:26])=[C:24]([O:30][CH3:31])[CH:23]=1.CN1CCCC1=O.C(=O)([O-])O.[Na+]>C(OCC)(=O)C>[Br:21][C:22]1[CH:28]=[C:27]([CH3:29])[C:25]([NH:26][C:2]2[N:6]([CH3:7])[C:5]3[C:8]([N:12]4[C:16]([CH2:17][CH3:18])=[CH:15][C:14]([CH2:19][CH3:20])=[N:13]4)=[CH:9][CH:10]=[CH:11][C:4]=3[N:3]=2)=[C:24]([O:30][CH3:31])[CH:23]=1

Participants

6

Reactant 4

HCID 13387N-methyl-2-pyrrolidoneHCID 516892Sodium BicarbonateHCID 106802184-Bromo-2-methoxy-6-methylanilineHCID 672730482-chloro-7-(3,5-diethyl-1H-pyrazol-1-yl)-1-methyl-1H-benzimidazole

Product 1

HCID 11977537N-(4-Bromo-2-methoxy-6-methylphenyl)-7-(3,5-diethyl-1H-pyrazol-1-yl)-1-methyl-1H-benzimidazol-2-amineYield 83.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 83 mg (0.287 mmol) of 2-chloro-7-(3,5-diethyl-1H-pyrazol-1-yl)-1-methyl-1H-benzimidazole, 186 mg (0.862 mmol) of 4-bromo-2-methoxy-6-methylaniline and 0.15 mL of 1-methyl-2-pyrrolidinone was stirred at 110° C. for 20 hours. After cooling, the reaction mixture was neutralized with saturated aqueous sodium hydrogen carbonate, followed by addition of ethyl acetate. The resulting crystals were collected by filtration and washed with water and ethyl acetate to give 112 mg (83%) of the title compound.

Workup

  1. temperatureAfter cooling
  2. filtrationThe resulting crystals were collected by filtration
  3. washwashed with water and ethyl acetate

Sources & evidence

ORD record
ord-ae637b6eed7a4798a98452e447e143e3
Source dataset
uspto-grants-2012_04
Patent number
US08163935B2

Reaction notes

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