Stannous Chloride → HCID 11552277, compound

HRID 969857Notes

Reaction equation

HRID 969857 reaction equation
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[CH:3]([NH:9][C:10]([C:12]1[CH:13]=[CH:14][CH:15]=[C:16]3[O:20][C:19]([C:21]4[CH:26]=[CH:25][C:24]([N+:27]([O-])=O)=[CH:23][CH:22]=4)=[N:18][C:17]=13)=[O:11])[CH2:2]2.[Sn](Cl)Cl>C(O)C>[N:1]12[CH2:6][CH2:5][CH:4]([CH2:7][CH2:8]1)[CH:3]([NH:9][C:10]([C:12]1[CH:13]=[CH:14][CH:15]=[C:16]3[O:20][C:19]([C:21]4[CH:22]=[CH:23][C:24]([NH2:27])=[CH:25][CH:26]=4)=[N:18][C:17]=13)=[O:11])[CH2:2]2

Participants

4

Reactant 2

HCID 24479Stannous ChlorideHCID 11661129HCID 11661129, compound

Product 1

HCID 11552277HCID 11552277, compoundYield 32.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of N-(1-azabicyclo[2.2.2]oct-3-yl)-2-(4-nitrophenyl)benzoxazole-4-carboxamide (24 mg 0.06 mmol) in ethanol was added tin(II) chloride (116 mg, 0.61 mmol). The reaction mixture was then heated to reflux for 4 h. The reaction was cooled down to room temperature, then concentrated. The residue was dissolved in ethyl acetate (10 mL). The resulting solution was washed with 1 N NaOH (12 mL), water and brine, dried (Na2SO4), filtered and concentrated. The crude material was purified by column chromatography (silica gel, 90:9:1 ethyl acetate/methanol/concentrated ammonium hydroxide) to afford N-(1-azabicyclo[2.2.2]oct-3-yl)-2-(4-aminophenyl)benzoxazole-4-carboxamide (7 mg, 2%) as a yellow solid: 1H NMR (500 MHz, CDCl3) δ 9.68 (d, J=6.5 Hz, 1H), 8.13 (d, J=8.0 Hz, 1H), 8.02 (d, J=8.5 Hz, 2H), 7.65 (d, J=8.0 Hz, 1H), 7.39 (t, J=8.0 Hz, 1H), 6.79 (d, J=8.5 Hz, 2H), 4.40-4.36 (m, 1H), 4.19-4.16 (m, 3H), 3.20-2.90 (m, 5H), 2.30-0.80 (m, 5H); MS (ESI+) m/z 363 (M+H); HPLC 96.0% (AUC), tR=12.35 min.

Workup

  1. temperatureThe reaction mixture was then heated
  2. temperatureto reflux for 4 h
  3. concentrationconcentrated
  4. dissolutionThe residue was dissolved in ethyl acetate (10 mL)
  5. washThe resulting solution was washed with 1 N NaOH (12 mL), water and brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude material was purified by column chromatography (silica gel, 90:9:1 ethyl acetate/methanol/concentrated ammonium hydroxide)

Sources & evidence

ORD record
ord-e5a9a252ae4847d0a46ab1f29dccd45a
Source dataset
uspto-grants-2007_12
Patent number
US07307094B2

Reaction notes

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