Methanol → 3-[5,6-Dimethyl-3-(4-methyl-benzo[b]thiophen-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-3-ethoxy-propionic acid ethyl ester

HRID 1747306Notes

Reaction equation

HRID 1747306 reaction equation
[CH3:1][C:2]1[C:22]([CH3:23])=[CH:21][C:5]2[N:6]([CH2:10][C:11]3[C:12]4[C:19]([CH3:20])=[CH:18][CH:17]=[CH:16][C:13]=4[S:14][CH:15]=3)[C:7](=[O:9])[NH:8][C:4]=2[CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH2:30]([O:32][CH:33]=[CH:34][C:35]([O:37][CH2:38][CH3:39])=[O:36])[CH3:31].CO>C(OCC)(=O)C>[CH2:38]([O:37][C:35](=[O:36])[CH2:34][CH:33]([N:8]1[C:4]2[CH:3]=[C:2]([CH3:1])[C:22]([CH3:23])=[CH:21][C:5]=2[N:6]([CH2:10][C:11]2[C:12]3[C:19]([CH3:20])=[CH:18][CH:17]=[CH:16][C:13]=3[S:14][CH:15]=2)[C:7]1=[O:9])[O:32][CH2:30][CH3:31])[CH3:39]

Participants

6

Reactant 4

HCID 887MethanolHCID 11430Potassium CarbonateHCID 221780Ethyl 3-ethoxy-2-propenoateHCID 673605475,6-Dimethyl-1-(4-methyl-benzo[b]thiophen-3-ylmethyl)-1,3-dihydro-benzimidazol-2-one

Product 1

HCID 675430833-[5,6-Dimethyl-3-(4-methyl-benzo[b]thiophen-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-3-ethoxy-propionic acid ethyl esterYield 31.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
130 °C

Procedure

To a mixture of 5,6-Dimethyl-1-(4-methyl-benzo[b]thiophen-3-ylmethyl)-1,3-dihydro-benzimidazol-2-one (0.1 g, 0.31 mmol) and K2CO3 (86 mg, 0.62 mmol) in a microwave vial was added Ethyl 3-ethoxyacrylate (0.45 g, 3.1 mmol). The reaction mixture was heated to 130° C. for 20 min in a microwave. The reaction mixture was then diluted with ethyl acetate (since there was some insoluble material left, MeOH was added to the solution mixture to solubilize the material). This organic phase was washed with water (×2). The organic phase was dried over Na2SO4 and concentrated. The resulting residue was purified by silica gel prep TLC using 4:1 Hexane:ethyl acetate as an eluent to afford 45 mg of the desired product as an oily foam. LCMS (ESMS): m/z 467.32 (M+H+).

Workup

  1. waitleft
  2. washThis organic phase was washed with water (×2)
  3. dry with materialThe organic phase was dried over Na2SO4
  4. concentrationconcentrated
  5. customThe resulting residue was purified by silica gel prep TLC

Sources & evidence

ORD record
ord-34645005c1704b1faad1a703244edd7f
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

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