Trifluoroacetic acid → HCID 25110308, compound

HRID 710372Notes

Reaction equation

HRID 710372 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:13]2[O:17][N:16]=[C:15]([C:18]3[CH:26]=[CH:25][CH:24]=[C:23]4[C:19]=3[CH:20]=[CH:21][NH:22]4)[N:14]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH2:11][CH3:12])[CH3:2].C1COCC1.C(C(O)=O)(F)(F)F>>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:13]2[O:17][N:16]=[C:15]([C:18]3[CH:26]=[CH:25][CH:24]=[C:23]4[C:19]=3[CH2:20][CH2:21][NH:22]4)[N:14]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH2:11][CH3:12])[CH3:2]

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 8028TetrahydrofuranHCID 251102975-(3,4-Diethoxyphenyl)-3-(1H-indol-4-yl)-1,2,4-oxadiazole

Product 1

HCID 25110308HCID 25110308, compoundYield 43%

Procedure

To a solution of the product of Step B (0.06 g; 0.172 mmol) in 1M BH3 in THF (0.35 ml; 0.35 mmol) CF3CO2H (0.4 ml) was added drop wise at 0° C. with stirring. After the addition was completed (˜5 min) the reaction was quenched with H2O (0.5 ml) and solvents were removed under reduced pressure. The residue was diluted to 10 ml with EtOAc and was washed with 10% NaOH (2×2 ml), brine and dried over anhydrous MgSO4 and filtered. The filtrate was evaporated to dryness under reduced pressure to give the title compound (0.026 g; 43%) as a creamy foam, which was used in the next step without further purification. 1H-NMR (CDCl3) 1.49 (m, 6H); 1.7 (broad s, 1H+H2O); 3.45 (tr, 2H, J=8.9 Hz); 3.65 (tr, 2H, J=8.9 Hz); 4.19 (m, 4H); 6.75 (d, 1H, J=7.7 Hz); 6.97 (d, 1H, J=8.5 Hz); 7.17 (tr, 1H, J=7.7); 7.52 (d, 1H, J=7.2 Hz); 7.68 (d, 1H, J=1.9 Hz); 7.78 (dd, 1H, J=1.9, 7.2 Hz).

Workup

  1. additionAfter the addition
  2. custom(˜5 min)
  3. customwas quenched with H2O (0.5 ml) and solvents
  4. customwere removed under reduced pressure
  5. additionThe residue was diluted to 10 ml with EtOAc
  6. washwas washed with 10% NaOH (2×2 ml), brine
  7. dry with materialdried over anhydrous MgSO4
  8. filtrationfiltered
  9. customThe filtrate was evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-428fcbea53184b4cbbe3a9c346ad221f
Source dataset
uspto-grants-2015_11
Patent number
US09181182B2

Reaction notes

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