Dichloromethane → HCID 66812294, compound

HRID 1097852Notes

Reaction equation

HRID 1097852 reaction equation
[CH3:1][O:2][C:3](=[O:24])[CH:4]=[CH:5][C:6]1[CH:23]=[CH:22][C:9]2[N:10]([CH2:15][CH2:16][N:17]([CH2:20][CH3:21])[CH2:18][CH3:19])[C:11]([CH2:13][NH2:14])=[N:12][C:8]=2[CH:7]=1.C(N(CC)C(C)C)(C)C.ClCCl.[CH3:37][C:38]([CH3:43])([CH3:42])[C:39](Cl)=[O:40]>C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:24])[CH:4]=[CH:5][C:6]1[CH:23]=[CH:22][C:9]2[N:10]([CH2:15][CH2:16][N:17]([CH2:20][CH3:21])[CH2:18][CH3:19])[C:11]([CH2:13][NH:14][C:39](=[O:40])[C:38]([CH3:43])([CH3:42])[CH3:37])=[N:12][C:8]=2[CH:7]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 62493Pivaloyl chlorideHCID 81531DiisopropylethylamineHCID 66811963HCID 66811963, compound

Product 1

HCID 66812294HCID 66812294, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a pre-stirred solution of 3-[2-aminomethyl-1-(2-diethylamino-ethyl)-1H-benzoimidazol-5-yl]-acrylic acid methyl ester (61-6, 0.10 g, 0.23 mmol), N,N-diisopropylethylamine (97 μL, 0.58 mmol) and dichloromethane (1.17 mL) was added 2,2-dimethyl-propionyl chloride (34.6 μL, 0.28 mmol) and the resulting reaction mixture was stirred at room temperature for 1 h. When the reaction has completed, ethyl acetate (20 mL) was added to dilute the mixture. The organic contents were washed with saturated sodium hydrogencarbonate (2×20 mL) and brine (2×20 mL), before drying in Na2SO4. The mixture was filtered and concentrated in vacuo. The product 3-{1-(2-diethylamino-ethyl)-2-[(2,2-dimethyl-propionylamino)-methyl]-1H-benzoimidazol-5-yl}-acrylic acid methyl ester (61-7) was obtained in 76.6% (74.1 mg). LCMS m/z: 415 ([M+H]+).

Workup

  1. customthe resulting reaction mixture
  2. additionto dilute the mixture
  3. washThe organic contents were washed with saturated sodium hydrogencarbonate (2×20 mL) and brine (2×20 mL)
  4. dry with materialbefore drying in Na2SO4
  5. filtrationThe mixture was filtered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-676ccc0fef664e77969bc3f84628b1e9
Source dataset
uspto-grants-2012_03
Patent number
US08143282B2

Reaction notes

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