Triethylamine → 6-(2-Chlorophenyl)-5-(4-chlorophenyl)-N,N-diethyl-3-[(trifluoroacetyl)amino]-furo[2,3-b]pyridine-2-carboxamide

HRID 8821Notes

Reaction equation

HRID 8821 reaction equation
[CH2:1]([N:3](CC)[CH2:4][CH3:5])[CH3:2].C[Al](C)C.[Cl:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[C:19]1[N:24]=[C:23]2[O:25][C:26]([C:35](OCC)=[O:36])=[C:27]([NH:28][C:29](=[O:34])[C:30]([F:33])([F:32])[F:31])[C:22]2=[CH:21][C:20]=1[C:40]1[CH:45]=[CH:44][C:43]([Cl:46])=[CH:42][CH:41]=1>C1(C)C=CC=CC=1.C(Cl)Cl>[Cl:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[C:19]1[N:24]=[C:23]2[O:25][C:26]([C:35]([N:3]([CH2:4][CH3:5])[CH2:1][CH3:2])=[O:36])=[C:27]([NH:28][C:29](=[O:34])[C:30]([F:33])([F:32])[F:31])[C:22]2=[CH:21][C:20]=1[C:40]1[CH:41]=[CH:42][C:43]([Cl:46])=[CH:44][CH:45]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 16682925TrimethylaluminumHCID 21984923HCID 21984923, compound

Product 1

HCID 219849286-(2-Chlorophenyl)-5-(4-chlorophenyl)-N,N-diethyl-3-[(trifluoroacetyl)amino]-furo[2,3-b]pyridine-2-carboxamide

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 6344DichloromethaneSolvent

Procedure

To a magnetically stirred solution of 0.119 mL (1.15 mmol) of triethylamine in 5 mL toluene was added 0.575 mL (1.15 mmol) of a 2.0 M solution of trimethylaluminum in toluene at 0° C. The reaction mixture was allowed to warm to room temperature and was stirred for 30 min. A solution of 0.300 g (0.57 mmol) of the product of Example 181 in 1 mL CH2Cl2 was added to the reaction mixture and when the addition was complete the reaction mixture was heated at 60° C. for 2 h. The reaction mixture was allowed to cool again to room temperature and was partitioned between EtOAc and 10% aq. NaHSO4. The organic extracts were combined, washed with water and brine, dried (Na2SO4), filtered and evaporated. The residue was purified on a silica gel flash chromatography column eluted with 0–30% EtOAc-hexane. Evaporation of the purified fractions and drying in vacuo afforded the titled compound. HPLC/MS: 550.0 (M+1), 551.8 (M+3); Rt=4.74 min.

Workup

  1. additionthe addition
  2. temperaturewas heated at 60° C. for 2 h
  3. temperatureto cool again to room temperature
  4. customwas partitioned between EtOAc and 10% aq. NaHSO4
  5. washwashed with water and brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified on a silica gel flash chromatography column
  10. washeluted with 0–30% EtOAc-hexane
  11. customEvaporation of the purified fractions
  12. customdrying in vacuo

Sources & evidence

ORD record
ord-4e819361b5db4ebbb47b90be7f1b7076
Source dataset
uspto-grants-2006_08
Patent number
US07091216B2

Reaction notes

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