Sodium Hydroxide → HCID 21914113, compound

HRID 551407Notes

Reaction equation

HRID 551407 reaction equation
[CH:1]([CH:3]1[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]1[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=O.[C:19]([O-])(=O)[CH3:20].[NH4+:23].[OH-].[Na+]>C(O)(=O)C>[CH3:1][C:3]1[NH:4][C:1]([CH:3]2[CH2:11][C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[N:4]2[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[N:23][C:11]=1[CH2:10][CH2:19][CH3:20]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 517165Ammonium AcetateHCID 21914148HCID 21914148, compound

Product 1

HCID 21914113HCID 21914113, compoundYield 255.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Intermediate (12) (0.00101 mole), 2-3-hexanedione (0.004 mole), and ammonium acetate (0.025 mole) were combined in acetic acid (4 ml), and immediately placed on a steam bath for 15 minutes. After 2 hours at room temperature, the reaction was poured into ice water (100 ml), basified with 3N NaOH, and extracted with diethylether (twice). The organic phases were combined, dried, filtered, and concentrated. The residue was taken up in diethylether, concentrated and then purified by prep LC, yielding 0.440 g of 1,1-dimethylethyl 2,3-dihydro-2-(5-methyl-4-propyl-1H-imidazol-2-yl)-1H-indole-1-carboxylate (compound 99).

Workup

  1. waitAfter 2 hours at room temperature
  2. extractionextracted with diethylether (twice)
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. concentrationconcentrated
  7. custompurified by prep LC

Sources & evidence

ORD record
ord-5e436a2611b64396ade2eea34bd3e692
Source dataset
uspto-grants-2011_05
Patent number
US07947713B2

Reaction notes

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