Hydrochloric Acid → methyl 3-cyclohexyl-2-{4-methoxy-2-[(methylamino)methyl]phenyl}-1-(2-oxoethyl)-1H-indole-6-carboxylate

HRID 1713998Notes

Reaction equation

HRID 1713998 reaction equation
Cl.[CH:2]1([C:8]2[C:16]3[C:11](=[CH:12][C:13]([C:17]([O:19][CH3:20])=[O:18])=[CH:14][CH:15]=3)[N:10]([CH2:21][CH:22]3OCC[O:23]3)[C:9]=2[C:27]2[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][C:28]=2[CH2:35][NH:36][CH3:37])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1>C1COCC1>[CH:2]1([C:8]2[C:16]3[C:11](=[CH:12][C:13]([C:17]([O:19][CH3:20])=[O:18])=[CH:14][CH:15]=3)[N:10]([CH2:21][CH:22]=[O:23])[C:9]=2[C:27]2[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][C:28]=2[CH2:35][NH:36][CH3:37])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68505892HCID 68505892, compound

Product 1

HCID 86604963methyl 3-cyclohexyl-2-{4-methoxy-2-[(methylamino)methyl]phenyl}-1-(2-oxoethyl)-1H-indole-6-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Aqueous HCl (25 eq, 3 M) was added to a solution of methyl 3-cyclohexyl-1-(1,3-dioxolan-2-ylmethyl)-2-{4-methoxy-2-[(methylamino)methyl]phenyl}-1H-indole-6-carboxylate in THF (0.02 M), and the mixture heated at reflux for 24 h. The volatiles were reduced in vacuo, and the residue partitioned between EtOAc and saturated aqueous NaHCO3 (ensuring that the aqueous phase is basic). The aqueous phase was extracted with EtOAc and the combined organics washed with water and brine, before being dried (Na2SO4), filtered and concentrated in vacuo to give the title compound in essentially quantitative yield; MS (ES+) m/z 449 (M+H)+.

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 24 h
  3. customthe residue partitioned between EtOAc and saturated aqueous NaHCO3 (
  4. extractionThe aqueous phase was extracted with EtOAc
  5. washthe combined organics washed with water and brine
  6. dry with materialbefore being dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d287052ce69a4ce79db6aedab5656cf3
Source dataset
uspto-grants-2010_09
Patent number
US07795247B2

Reaction notes

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