Triethylamine → HCID 178509447, compound

HRID 2360838Notes

Reaction equation

HRID 2360838 reaction equation
FC(F)(F)C(OC(=O)C(F)(F)F)=O.[NH:14]1[C:18]2[CH:19]=[CH:20][C:21]([C:23]([N:25]3[C@@H:34]4[C@@H:29]([C:30]5[CH:38]=[CH:37][C:36]([C:39]([NH2:41])=O)=[CH:35][C:31]=5[CH2:32][CH2:33]4)[CH2:28][CH2:27][CH2:26]3)=[O:24])=[CH:22][C:17]=2[N:16]=[CH:15]1.C(N(CC)CC)C>ClCCl>[NH:14]1[C:18]2[CH:19]=[CH:20][C:21]([C:23]([N:25]3[C@@H:34]4[C@@H:29]([C:30]5[CH:38]=[CH:37][C:36]([C:39]#[N:41])=[CH:35][C:31]=5[CH2:32][CH2:33]4)[CH2:28][CH2:27][CH2:26]3)=[O:24])=[CH:22][C:17]=2[N:16]=[CH:15]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 178513515HCID 178513515, compound

Product 1

HCID 178509447HCID 178509447, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic anhydride (0.4 mL) is added to a solution of cis-4-(1H-benzoimidazole-5-carbonyl)-1,2,3,4,4a,5,6,10b-octahydro-benzo[f]quinoline-8-carboxylic acid amide (140 mg) and triethylamine (0.6 mL) in dichloromethane (4 mL) chilled in an ice bath. The cooling bath is removed and the solution is stirred at room temperature for 3 h. Another portion of trifluoroacetic anhydride (0.4 mL) and triethylamine (0.6 mL) are then added and stirring is continued at 35° C. overnight. The solution is diluted with dichloromethane and washed with water and brine. After drying (MgSO4), the solvent is evaporated and the residue is chromatographed on silica gel (dichloromethane/methanol 20:1→1:1) to furnish the title compound as a yellowish solid. Yield: 50 mg (38% of theory); Mass spectrum (ESI+): m/z=357 [M+H]+.

Workup

  1. temperaturechilled in an ice bath
  2. customThe cooling bath is removed
  3. additionAnother portion of trifluoroacetic anhydride (0.4 mL) and triethylamine (0.6 mL) are then added
  4. stirringstirring
  5. waitis continued at 35° C. overnight
  6. additionThe solution is diluted with dichloromethane
  7. washwashed with water and brine
  8. dry with materialAfter drying (MgSO4)
  9. customthe solvent is evaporated
  10. customthe residue is chromatographed on silica gel (dichloromethane/methanol 20:1→1:1)

Sources & evidence

ORD record
ord-a8a8520bbe74466a8cedcfb2de167387
Source dataset
uspto-grants-2014_04
Patent number
US08686149B2

Reaction notes

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