Stannous chloride dihydrate → HCID 59457791, compound

HRID 1711783Notes

Reaction equation

HRID 1711783 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[N:14]([C:15]=2[C:16]2[CH:17]=[CH:18][C:19]4[N+:23]([O-])=[C:22]([C:25]5[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=5)[NH:21][C:20]=4[CH:31]=2)[CH:13]=[CH:12][O:11]3)=[CH:4][CH:3]=1.O.O.[Sn](Cl)Cl.C([O-])(O)=O.[Na+].N([O-])=O.[Na+]>O.CCO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[N:14]([C:15]=2[C:16]2[CH:17]=[CH:18][C:19]4[N:23]=[C:22]([C:25]5[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=5)[NH:21][C:20]=4[CH:31]=2)[CH:13]=[CH:12][O:11]3)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 61436Stannous chloride dihydrateHCID 516892Sodium BicarbonateHCID 23668193Sodium NitriteHCID 178526226HCID 178526226, compound

Product 1

HCID 59457791HCID 59457791, compoundYield 67.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 6-[6-(4-fluorophenyl)-imidazo[2,1-b]oxazol-5-yl]-2-pyridin-4-yl-1H-benzoimidazole 3-oxide (0.26 g, 0.56 mmol), tin(II) chloride dihydrate (0.64 g, 2.8 mmol) and EtOH (5.5 mL) was heated at about 70° C. for about 18 h. The reaction was poured over ice then the pH was adjusted to 8 with saturated aqueous NaHCO3 and filtered to remove tin salts. The filter cake was stirred with EtOAc (3×30 mL) then filtered. Each organic filtrate was then used to extract the initial aqueous filtrate. The combined organic layers were washed with brine, dried over Na2SO4, decanted, and concentrated. To the crude material was added 6 M HCl in water (0.94 mL; VWR). The reaction was cooled to about 0° C. and then NaNO2 (0.058 g, 0.85 mmol) in water (0.53 mL) was added dropwise. After about 2 h, no reaction was seen by LC-MS. The reaction was filtered, washing with water, and dried in the vacuum oven at 55-65° C. to give the title compound (0.15 g, 64%): LC/MS (Table 1, Method b) Rt, =1.82 min; MS m/z: 396.2 (M+H)+.

Workup

  1. additionThe reaction was poured over ice
  2. filtrationfiltered
  3. customto remove tin salts
  4. filtrationthen filtered
  5. extractionto extract the initial aqueous filtrate
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over Na2SO4
  8. customdecanted
  9. concentrationconcentrated
  10. additionTo the crude material was added 6 M HCl in water (0.94 mL; VWR)
  11. temperatureThe reaction was cooled to about 0° C.
  12. filtrationThe reaction was filtered
  13. washwashing with water
  14. customdried in the vacuum oven at 55-65° C.

Sources & evidence

ORD record
ord-cc773d2ec0f0453785a404627956130d
Source dataset
uspto-grants-2010_09
Patent number
US07790741B2

Reaction notes

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