Dimethylformamide → HCID 10224959, compound

HRID 1070864Notes

Reaction equation

HRID 1070864 reaction equation
[CH3:1][O:2][C:3](=[O:27])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:11]=[CH:12][C:13]2[N:17]=[C:16](Cl)[N:15]([C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=3)[C:14]=2[CH:26]=1.CN(C)C=O.[NH:33]1[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1>O>[CH3:1][O:2][C:3](=[O:27])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:11]=[CH:12][C:13]2[N:17]=[C:16]([N:33]3[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]3)[N:15]([C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=3)[C:14]=2[CH:26]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 8082Piperidine2×HCID 69435062HCID 69435062, compound

Product 1

HCID 10224959HCID 10224959, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

240 mg of 6-[[2-chloro-1-(4-methylphenyl)-1H-benzimidazol-6-yl]oxy]hexanoic acid methyl ester was mixed with 0.2 ml of N,N-dimethylformamide and 0.75 ml of piperidine, and the mixture was stirred for 7.5 hours at 110° C. Another 0.75 ml of piperidine was added, and it was heated for another 4 hours at 110° C. It was mixed with water, extracted with ethyl acetate, the organic phase was dried on sodium sulfate and concentrated by evaporation in a vacuum. The residue was purified by column chromatography on silica gel. 16 mg was obtained.

Workup

  1. temperatureit was heated for another 4 hours at 110° C
  2. extractionextracted with ethyl acetate
  3. customthe organic phase was dried on sodium sulfate
  4. concentrationconcentrated by evaporation in a vacuum
  5. customThe residue was purified by column chromatography on silica gel
  6. custom16 mg was obtained

Sources & evidence

ORD record
ord-65b7fe7843d04978b1be58726875a8eb
Source dataset
uspto-grants-2005_06
Patent number
US06903126B2

Reaction notes

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