Hydrochloric Acid → HCID 18669072, compound

HRID 1058973Notes

Reaction equation

HRID 1058973 reaction equation
[BH4-].[Li+].[Cl:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH2:13][C:14](OC)=[O:15])[C:8]([C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=1)=[C:7]2[CH2:25][CH2:26][C:27]([N:29]1[CH2:34][CH2:33][N:32]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=2[O:41][CH3:42])[CH2:31][CH2:30]1)=[O:28].Cl.C(=O)([O-])[O-].[K+].[K+]>C1COCC1.C1(C)C=CC=CC=1.C(OCC)(=O)C>[Cl:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH2:13][CH2:14][OH:15])[C:8]([C:18]1[CH:19]=[CH:20][C:21]([Cl:24])=[CH:22][CH:23]=1)=[C:7]2[CH2:25][CH2:26][C:27]([N:29]1[CH2:30][CH2:31][N:32]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=2[O:41][CH3:42])[CH2:33][CH2:34]1)=[O:28]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 4148881Lithium borohydrideHCID 44274316HCID 44274316, compound

Product 1

HCID 18669072HCID 18669072, compoundYield 51.3%

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Lithium borohydride (5 mg) was added in one portion to a solution of methyl 5-chloro-2-(4-chlorophenyl)-3-{3-[4-(2-methoxyphenyl)piperazin-1-yl]-3-oxoprop-1-yl}-1H-indole-1-acetate (Example 140, 43 mg) in THF (2 mL) and toluene (1 mL) and the mixture was stirred at room temperature for 15 min., then at 60° C. for 45 min. The mixture was cooled, hydrochloric acid (1M, 2 mL) was added and the mixture was stirred at room temperature for 10 min. Potassium carbonate and ethyl acetate (30 mL) were added and the layers were separated. The organic phase was dried (Na2SO4) and the solvent was evaporated under reduced pressure. The residue was recrystallised from ethyl acetate and the solid was collected and dried in vacuo to give the title compound as a colorless solid (21 mg). m/z (ES+) 552, 554 (M+1).

Workup

  1. waitat 60° C. for 45 min
  2. temperatureThe mixture was cooled
  3. stirringthe mixture was stirred at room temperature for 10 min
  4. customthe layers were separated
  5. dry with materialThe organic phase was dried (Na2SO4)
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was recrystallised from ethyl acetate
  8. customthe solid was collected
  9. customdried in vacuo

Sources & evidence

ORD record
ord-aaea659259004471a288d1a9d4638220
Source dataset
uspto-grants-2003_02
Patent number
US06518273B1

Reaction notes

Loading…