Hydrochloric Acid → HCID 67344694, compound

HRID 1669415Notes

Reaction equation

HRID 1669415 reaction equation
[CH:1]1([C:7]2[C:15]3[C:10](=[CH:11][C:12]([C:16]([O:18][CH3:19])=[O:17])=[CH:13][CH:14]=3)[NH:9][C:8]=2[C:20]2[CH:25]=[CH:24][C:23]([O:26][CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=3)=[CH:22][C:21]=2[O:34]COC)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl>CO>[CH:1]1([C:7]2[C:15]3[C:10](=[CH:11][C:12]([C:16]([O:18][CH3:19])=[O:17])=[CH:13][CH:14]=3)[NH:9][C:8]=2[C:20]2[CH:25]=[CH:24][C:23]([O:26][CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=3)=[CH:22][C:21]=2[OH:34])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67343530HCID 67343530, compound

Product 1

HCID 67344694HCID 67344694, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
80 °C

Procedure

Methyl 3-cyclohexyl-2-[2-(methoxymethoxy)-4-(pyridin-2-ylmethoxy)phenyl]-1H-indole-6-carboxylate was dissolved in MeOH (0.5 M). 3N HCl (2 eq) was added, followed by more MeOH. The mixture was warmed to 80° C. for 6 h. By this time a clear solution had formed. All volatiles were evaporated in vacuo and the residual material was dissolved in DCM. The solution was washed with sat. aq. NaHCO3 and brine. After drying over Na2SO4 all volatiles were evaporated in vacuo leaving a beige amorphous solid (quant). (ES+) m/z 457 (M+H)+.

Workup

  1. customBy this time a clear solution had formed
  2. customAll volatiles were evaporated in vacuo
  3. dissolutionthe residual material was dissolved in DCM
  4. washThe solution was washed with sat. aq. NaHCO3 and brine
  5. dry with materialAfter drying over Na2SO4 all volatiles
  6. customwere evaporated in vacuo
  7. customleaving a beige amorphous solid (quant)

Sources & evidence

ORD record
ord-51e30e2620c848a8b85e0f49db930a61
Source dataset
uspto-grants-2011_08
Patent number
US07989438B2

Reaction notes

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