Dimethylformamide → HCID 117662400, compound

HRID 1428400Notes

Reaction equation

HRID 1428400 reaction equation
[Cl:1][C:2]1[C:20]([Cl:21])=[CH:19][C:5]2[NH:6][C:7]([CH2:9][N:10]([CH3:18])[C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[N:8][C:4]=2[CH:3]=1.CN(C=O)C.Br[CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30].C([O-])([O-])=O.[K+].[K+]>CCOC(C)=O>[C:13]([O:12][C:11]([N:10]([CH2:9][C:7]1[N:6]([CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])[C:5]2[CH:19]=[C:20]([Cl:21])[C:2]([Cl:1])=[CH:3][C:4]=2[N:8]=1)[CH3:18])=[O:17])([CH3:16])([CH3:14])[CH3:15]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 117660492HCID 117660492, compound

Product 1

HCID 117662400HCID 117662400, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

To a mixture of tert-butyl [(5,6-dichloro-1H-benzimidazol-2-yl)methyl]methylcarbamate (400 mg) and DMF (4 mL) were added ethyl bromoacetate (201 μL) and K2CO3 (335 mg), followed by heating and stirring at 70° C. for 2 hours. The reaction mixture was diluted with EtOAc, washed with water and brine in this order, dried over MgSO4, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: Hex/EtOAc=50/50-0/100) to obtain ethyl (2-{[(tert-butoxycarbonyl)(methyl)amino]methyl}-5,6-dichloro-1H-benzimidazol-1-yl)acetate (393 mg).

Workup

  1. temperatureby heating
  2. washwashed with water and brine in this order
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluent: Hex/EtOAc=50/50-0/100)

Sources & evidence

ORD record
ord-812a3aa9065648e594ea55b99e32d8c1
Source dataset
uspto-grants-2015_01
Patent number
US08937087B2

Reaction notes

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