Trifluoroacetic acid → HCID 51346963, compound

HRID 2175035Notes

Reaction equation

HRID 2175035 reaction equation
FC(F)(F)C(O)=O.[C:8]1([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]([N:16]1[CH:23]2[CH:18]([CH2:19][CH2:20][NH:21][CH2:22]2)[CH2:17]1)=[O:15].Cl[C:31]1[CH:40]=[N:39][C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[N:32]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[C:8]1([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]([N:16]1[CH:23]2[CH:18]([CH2:19][CH2:20][N:21]([C:31]3[CH:40]=[N:39][C:38]4[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=4)[N:32]=3)[CH2:22]2)[CH2:17]1)=[O:15]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 2389382-ChloroquinoxalineHCID 67086667HCID 67086667, compound2×

Product 1

HCID 51346963HCID 51346963, compoundYield 40.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of trifluoro acetic acid salt of biphenyl-2-yl-(3,8-diaza-bicyclo[4.2.0]oct-8-yl)-methanone (Intermediate 3, 122.0 mg, 0.3 mmol), 2-chloro quinoxaline (60.0 mg, 0.36 mmol), K2CO3 (166 mg, 4 mmol) in DMF (7 mL) was stirred at 80° C. for 18 h. The reaction mixture was partitioned between ethyl acetate (25 mL) and water (120 mL). The organic layers were washed with water (2×30 mL), combined, dried (Na2SO4), filtered and concentrated. The crude residue was purified on HPLC (basic system) to yield the title compound (51 mg, 40%). MS (ESI) mass calcd. for C27H24N4O, 420.51; m/z found, 421 [M+H]+. 1H NMR (CDCl3): 8.44 (s, 0.55H), 8.17 (s, 0.45H), 7.97-7.87 (m, 1H), 7.76-7.71 (m, 0.5H), 7.65-7.50 (m, 2H), 7.48-7.30 (m, 7H), 7.09-6.94 (m, 2H), 7.20-7.12 (m, 0.5H), 4.78-4.49 (m, 1H), 4.02-3.78 (m, 1H), 3.76-3.58 (m, 2H), 3.55-3.48 (m, 0.5H), 3.32-3.23 (m, 0.5H), 3.15-2.97 (m, 1H), 2.74-2.39 (m, 1H), 2.12-1.54 (m, 3H).

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate (25 mL) and water (120 mL)
  2. washThe organic layers were washed with water (2×30 mL)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude residue was purified on HPLC (basic system)

Sources & evidence

ORD record
ord-ac8dc4ef6c4d48729ca07533eba9c672
Source dataset
uspto-grants-2015_06
Patent number
US09062044B2

Reaction notes

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