Potassium Carbonate → 3-[3-(1,4-Dimethyl-1H-indol-3-ylmethyl)-5,6-dimethyl-2-oxo-2,3-dihydro-benzimidazol-1-yl]-hexanoic acid ethyl ester

HRID 1747304

Reaction equation

HRID 1747304 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[C:6]([CH3:11])[CH:7]=[CH:8][CH:9]=2)[C:4]([CH2:12][N:13]2[C:17]3[CH:18]=[C:19]([CH3:23])[C:20]([CH3:22])=[CH:21][C:16]=3[NH:15][C:14]2=[O:24])=[CH:3]1.C([O-])([O-])=O.[K+].[K+].CC(N(C)C)=O.[C:37]([O:44][CH2:45][CH3:46])(=[O:43])/[CH:38]=[CH:39]/[CH2:40][CH2:41][CH3:42]>C(OCC)(=O)C>[CH2:45]([O:44][C:37](=[O:43])[CH2:38][CH:39]([N:15]1[C:16]2[CH:21]=[C:20]([CH3:22])[C:19]([CH3:23])=[CH:18][C:17]=2[N:13]([CH2:12][C:4]2[C:5]3[C:10](=[CH:9][CH:8]=[CH:7][C:6]=3[CH3:11])[N:2]([CH3:1])[CH:3]=2)[C:14]1=[O:24])[CH2:40][CH2:41][CH3:42])[CH3:46]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 31374DimethylacetamideHCID 5364778Ethyl trans-2-hexenoate2×HCID 594974211-(1,4-Dimethyl-1H-indol-3-ylmethyl)-5,6-dimethyl-1,3-dihydro-benzimidazol-2-one

Product 1

HCID 594976683-[3-(1,4-Dimethyl-1H-indol-3-ylmethyl)-5,6-dimethyl-2-oxo-2,3-dihydro-benzimidazol-1-yl]-hexanoic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 1-(1,4-Dimethyl-1H-indol-3-ylmethyl)-5,6-dimethyl-1,3-dihydro-benzimidazol-2-one (0.1 g, 0.31 mmol), K2CO3 (87 mg, 0.63 mmol) and ethyl trans-2-hexenoate (0.45 g, 3.1 mmol) was heated to 130° C. for 20 min in a microwave. Since the starting material was not soluble in ethyl trans-2-hexenoate even after heating, DMA (2 mL) was added to the reaction mixture and heated again at 150° C. for 30 min. Although the un-reacted starting material was present, the reaction mixture was diluted with ethyl acetate and washed with water (×4). The organic phase was dried over Na2SO4 and concentrated. The resulting heterogeneous residue was purified by silica gel prep TLC using 4:1 hexanes:ethyl acetate as an eluent to afford 25 mg of the desired product as an oil. LCMS (ESMS): m/z 462.88 (M+H+).

Workup

  1. temperatureafter heating
  2. temperatureheated again at 150° C. for 30 min
  3. washwashed with water (×4)
  4. dry with materialThe organic phase was dried over Na2SO4
  5. concentrationconcentrated
  6. customThe resulting heterogeneous residue was purified by silica gel prep TLC

Sources & evidence

ORD record
ord-070016990bc84c339ee2f55ce7a48bd0
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Linked notes

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