Potassium Carbonate → HCID 59497398, compound

HRID 1747360Notes

Reaction equation

HRID 1747360 reaction equation
[CH2:1]([O:3][C:4](=[O:20])[CH2:5][CH:6]([N:10]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[NH:12][C:11]1=[O:19])[CH2:7][CH2:8][CH3:9])[CH3:2].[Cl:21][C:22]1[CH:30]=[CH:29][C:28]([CH2:31][N+](C)(C)C)=[C:27]2[C:23]=1[C:24]([CH3:38])=[C:25]([CH3:37])[N:26]2[CH3:36].[I-].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O.C(OCC)(=O)C>[CH2:1]([O:3][C:4](=[O:20])[CH2:5][CH:6]([N:10]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[N:12]([CH2:31][C:28]2[CH:29]=[CH:30][C:22]([Cl:21])=[C:23]3[C:27]=2[N:26]([CH3:36])[C:25]([CH3:37])=[C:24]3[CH3:38])[C:11]1=[O:19])[CH2:7][CH2:8][CH3:9])[CH3:2]

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 30165Iodide IonHCID 594972633-(2-Oxo-2,3-dihydro-benzoimidazol-1-yl)-hexanoic acid ethyl esterHCID 59497533HCID 59497533, compound

Product 1

HCID 59497398HCID 59497398, compoundYield 15%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

To a stirred solution of 3-(2-oxo-2,3-dihydro-benzimidazol-1-yl)-hexanoic acid ethyl ester (93 mg, 0.34 mmol) in DMF (10 ml) was added (4-chloro-1,2,3-trimethyl-1H-indol-7-ylmethyl)-trimethyl-ammonium; iodide (132 mg, 0.34 mmol) followed by potassium carbonate (140 mg, 1.01 mmol). The resulting mixture was warmed at 100° C. over night and cooled to ambient temperature. The reaction was diluted with water and ethyl acetate. The layers were separated and the organic phase was dried (MgSO4), filtered and concentrated to give the crude product. Purification via preparative TLC (1 mm silica gel, 20% EtOAc/hexanes) gave 25 mg (15%) of the desired product.

Workup

  1. temperaturecooled to ambient temperature
  2. customThe layers were separated
  3. dry with materialthe organic phase was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give the crude product
  7. customPurification via preparative TLC (1 mm silica gel, 20% EtOAc/hexanes)

Sources & evidence

ORD record
ord-12b159c4f00c45c79cb5db142acbd952
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

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