Stannous Chloride → HCID 44546126, compound

HRID 1958661Notes

Reaction equation

HRID 1958661 reaction equation
[Cl:1][C:2]1[CH:30]=[CH:29][C:5]([CH2:6][C:7]2[NH:8][C:9]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([CH3:28])[N:23]=3)=[C:10]([C:12]3[CH:13]=[C:14]4[C:19](=[CH:20][CH:21]=3)[N:18]=[CH:17][CH:16]=[CH:15]4)[N:11]=2)=[CH:4][C:3]=1[N+:31]([O-])=O.Cl[Sn]Cl>CO>[Cl:1][C:2]1[CH:30]=[CH:29][C:5]([CH2:6][C:7]2[NH:8][C:9]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([CH3:28])[N:23]=3)=[C:10]([C:12]3[CH:13]=[C:14]4[C:19](=[CH:20][CH:21]=3)[N:18]=[CH:17][CH:16]=[CH:15]4)[N:11]=2)=[CH:4][C:3]=1[NH2:31]

Participants

4

Reactant 2

HCID 24479Stannous ChlorideHCID 44545794HCID 44545794, compound

Product 1

HCID 44546126HCID 44546126, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
55 °C

Procedure

To a suspension of 6-(2-(4-chloro-3-nitrobenzyl)-5-(6-methylpyridin-2-yl)-1H-imidazol-4-yl)quinoline (Example 74, prepared according to the method described in US 2008/0319012 A1) (50 mg, 0.110 mmol) in MeOH (2 mL) was added SnCl2 (104 mg, 0.548 mmol) and the mixture was stirred at 55° C. After 2.5 hours, the reaction mixture was cooled to room temperature, concentrated under reduced pressure. The residue was diluted with H2O (5 mL), filtered, and the filtrate was washed with 2N HCl (5 mL) and neutralized by addition of 5N NaOH solution to pH 7˜8. The precipitate was filtered, washed with H2O and Et2O, and dried under vacuum for overnight. The precipitate was purified by MPLC on silica gel (MeOH:EA:CH2Cl2=1:20:80 (v/v) to 1:4:16 (v/v)), and on NH silica gel (MC) to afford the title compound (33.1 mg, 71%). 1H NMR (300 MHz, CDCl3) δ 2.50 (3H, s), 4.09 (2H, s), 6.66 (1H, dd), 6.68 (1H, s), 6.96 (1H, d), 7.19 (1H, d), 7.25 (1H, bs), 7.36-7.39 (1H, m), 7.40 (1H, dd), 7.96 (1H, d), 8.10 (1H, d), 8.15-8.16 (2H, m), 8.91 (1H, dd). MS (ESI) m/z 426 (MH+).

Workup

  1. customprepared
  2. temperaturethe reaction mixture was cooled to room temperature
  3. concentrationconcentrated under reduced pressure
  4. additionThe residue was diluted with H2O (5 mL)
  5. filtrationfiltered
  6. washthe filtrate was washed with 2N HCl (5 mL)
  7. additionneutralized by addition of 5N NaOH solution to pH 7˜8
  8. filtrationThe precipitate was filtered
  9. washwashed with H2O and Et2O
  10. customdried under vacuum for overnight
  11. customThe precipitate was purified by MPLC on silica gel (MeOH:EA:CH2Cl2=1:20:80 (v/v) to 1:4:16 (v/v))

Sources & evidence

ORD record
ord-49c41112d13b41c4ba2ae32ea0b25b1c
Source dataset
uspto-grants-2013_04
Patent number
US08410146B2

Reaction notes

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