Stannous Chloride → HCID 11691222, compound

HRID 1815489Notes

Reaction equation

HRID 1815489 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[C:5]([NH2:11])=[CH:4][C:3]=1[S:12][C:13]1[CH:18]=[CH:17][C:16](/[CH:19]=[CH:20]/[C:21]([N:23]2[CH2:28][CH2:27][N:26]([C:29](=[O:31])[CH3:30])[CH2:25][CH2:24]2)=[O:22])=[CH:15][C:14]=1[Cl:32].Cl[Sn]Cl>CCO>[Cl:1][C:2]1[CH:7]=[C:6]([NH2:8])[C:5]([NH2:11])=[CH:4][C:3]=1[S:12][C:13]1[CH:18]=[CH:17][C:16](/[CH:19]=[CH:20]/[C:21]([N:23]2[CH2:24][CH2:25][N:26]([C:29](=[O:31])[CH3:30])[CH2:27][CH2:28]2)=[O:22])=[CH:15][C:14]=1[Cl:32]

Participants

4

Reactant 2

HCID 24479Stannous ChlorideHCID 10696558HCID 10696558, compound

Product 1

HCID 11691222HCID 11691222, compoundYield 44.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of nitrobenzene from Example 144A (170 mg, 0.34 mmol) in 2 mL of EtOH was added SnCl2 (325 mg, 1.72 mmol). The mixture was then refluxed under nitrogen atmosphere for 2 hours. The reaction was allowed to cool to ambient temperature, quenched with sat. NaHCO3, extracted with EtOAc(2×20 mL). The combined organic layer was washed with brine, dried over Na2SO4, concentrated in vacuo. The residue was then purified on Gilson preparative HPLC as described in Example 38B to give the title compound (70 mg, 44% yield) as a light yellow solid. 1H NMR (d6-DMSO, 300 MHz) δ 2.04 (s, 3H), 3.42-3.80 (m, 8H), 4.84 (s, 2H), 5.32 (s, 2H), 6.51 (d, J=8.4 Hz, 1H), 6.78 (d, J=8.4 Hz, 2H), 7.26 (d, J=15.6 Hz, 1H), 7.41 (d, J=15.6 Hz, 1H), 7.48 (d, J=8.4 Hz, 1H), 7.95 (d, J=1.8 Hz, 1H). MS (APCI+) (M+H)+ at m/z 465, 467, 469, 471.

Workup

  1. temperatureThe mixture was then refluxed under nitrogen atmosphere for 2 hours
  2. customquenched with sat. NaHCO3
  3. extractionextracted with EtOAc(2×20 mL)
  4. washThe combined organic layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was then purified on Gilson preparative HPLC

Sources & evidence

ORD record
ord-8f0b409a7e8b4c0f9726cf0b305b0f98
Source dataset
uspto-grants-2005_04
Patent number
US06878700B1

Reaction notes

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