Water → HCID 59497406, compound

HRID 1747442Notes

Reaction equation

HRID 1747442 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].[I-].[Cl:22][C:23]1[CH:31]=[C:30]([Cl:32])[C:29]2[N:25]([C:26]([CH3:37])=[CH:27][C:28]=2[CH2:33]N(C)C)[CH:24]=1.C([O-])([O-])=O.[K+].[K+].O>CN(C=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]([CH2:33][C:28]2[CH:27]=[C:26]([CH3:37])[N:25]3[C:29]=2[C:30]([Cl:32])=[CH:31][C:23]([Cl:22])=[CH:24]3)[C:11]1=[O:19])[CH2:7][CH2:8][CH3:9])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 594972633-(2-Oxo-2,3-dihydro-benzoimidazol-1-yl)-hexanoic acid ethyl esterHCID 86645719HCID 86645719, compound2×

Product 1

HCID 59497406HCID 59497406, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-(2-Oxo-2,3-dihydro-benzimidazol-1-yl)-hexanoic acid ethyl ester (30 mg, 0.11 mmol) in DMF (10 mL) were added (6,8-Dichloro-3-methyl-indolizin-1-ylmethyl)-dimethyl-amine iodide, CAS: (6,8-Dichloro-3-methyl-indolizin-1-ylmethyl)-dimethyl-amine iodide (65 mg, 0.16 mmol). and K2CO3 (45 mg, 0.33 mmol) at room temperature under nitrogen atmosphere. The solution was heated to 100 C for 2 hours. The solution was cooled down and water was added. The solution was extracted with EtOAc and the combined organic layer was dried with MgSO4. The solution was filtered and the filtrate was concentrated. The residue was purified by CombiFlash with 20% EtOAc in Hexane as the eluent to afford the desirable product 3-[3-(6,8-Dichloro-3-methyl-indolizin-1-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-hexanoic acid ethyl ester (20 mg, 38%) as a yellow foam.

Workup

  1. customat room temperature
  2. temperatureThe solution was heated to 100 C for 2 hours
  3. temperatureThe solution was cooled down
  4. extractionThe solution was extracted with EtOAc
  5. dry with materialthe combined organic layer was dried with MgSO4
  6. filtrationThe solution was filtered
  7. concentrationthe filtrate was concentrated
  8. customThe residue was purified by CombiFlash with 20% EtOAc in Hexane as the eluent

Sources & evidence

ORD record
ord-e9934837212c4e78af687e28dfa88e39
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

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