Ethoxyacetic acid → HCID 68670853, compound

HRID 2047402Notes

Reaction equation

HRID 2047402 reaction equation
[CH2:1]([O:3][CH2:4][C:5]([OH:7])=O)[CH3:2].C1N=CN(C(N2C=NC=C2)=O)C=1.Cl.[CH3:21][N:22]1[C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=2[N:24]=[C:23]1[C:31]1[CH:32]=[C:33]([N:37]2[CH2:42][CH2:41][CH:40]([NH2:43])[CH2:39][CH2:38]2)[CH:34]=[CH:35][CH:36]=1.CCN(C(C)C)C(C)C>C(#N)C>[CH2:1]([O:3][CH2:4][C:5]([NH:43][CH:40]1[CH2:41][CH2:42][N:37]([C:33]2[CH:34]=[CH:35][CH:36]=[C:31]([C:23]3[N:22]([CH3:21])[C:26]4[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=4[N:24]=3)[CH:32]=2)[CH2:38][CH2:39]1)=[O:7])[CH3:2]

Participants

6

Reactant 4

HCID 12301Ethoxyacetic acidHCID 682631,1'-CarbonyldiimidazoleHCID 81531DiisopropylethylamineHCID 68671994HCID 68671994, compound

Product 1

HCID 68670853HCID 68670853, compoundYield 435%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

Method N—Step e To a solution of ethoxyacetic acid (0.05 mL, 0.49 mmol) in acetonitrile (3 mL) was added CDI as a stock solution (0.80 g, 0.49 mmol) and the resulting suspension was stirred at room temperature for 3 h. {1-[3-(1-Methyl-1H-benzoimidazol-2-yl)-phenyl]-piperidin-4-ylamine hydrochloride (0.13 g, 0.41 mmol) and DIPEA (0.07 mL, 0.41 mmol) were added and the resulting solution heated at 70° C. overnight. The reaction was then cooled to room temperature, the solvent removed under reduced pressure. The crude product was redissolved in dichloromethane (4 mL) and washed with saturated Na2CO3 solution (2 mL) and water (2 mL). The organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography (eluent: dichloromethane:MeOH, gradient from 100% dichloromethane to 95% dichloromethane:5% MeOH) to afford 0.70 g (44%) of the title compound.

Workup

  1. additionwere added
  2. temperatureThe reaction was then cooled to room temperature
  3. customthe solvent removed under reduced pressure
  4. dissolutionThe crude product was redissolved in dichloromethane (4 mL)
  5. washwashed with saturated Na2CO3 solution (2 mL) and water (2 mL)
  6. dry with materialThe organic layer was dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by flash chromatography (eluent: dichloromethane:MeOH, gradient from 100% dichloromethane to 95% dichloromethane:5% MeOH)

Sources & evidence

ORD record
ord-eb035dde82e1488abe550ce0d91ad844
Source dataset
uspto-grants-2013_11
Patent number
US08592463B2

Reaction notes

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