Ethyl Acetate → HCID 135804635, compound

HRID 2182380Notes

Reaction equation

HRID 2182380 reaction equation
[N+:1]([C:4]1[CH:21]=[CH:20][C:7]2[NH:8][C:9]([C:11]3[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[NH:13][N:12]=3)=[N:10][C:6]=2[CH:5]=1)([O-])=O.[Sn](Cl)(Cl)(Cl)Cl.C(=O)(O)[O-].[Na+].C(OCC)(=O)C>CO.C(N(CC)CC)C>[NH:13]1[C:14]2[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:11]([C:9]2[NH:10][C:6]3[CH:5]=[C:4]([NH2:1])[CH:21]=[CH:20][C:7]=3[N:8]=2)=[N:12]1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 24287Tin tetrachlorideHCID 516892Sodium BicarbonateHCID 178526478HCID 178526478, compound

Product 1

HCID 135804635HCID 135804635, compoundYield 1,019.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8471TriethylamineSolvent

Procedure

A stirred solution of 3-(5-nitro-1H-benzoimidazol-2-yl)-1H-indazole [90.8 mg, Reference Example 233(as)] in methanol (1 ml) was treated with tin chloride (616 mg). The reaction was heated at reflux for 16 hours and then cooled to ambient temperature. The pH of the reaction mixture was adjusted to pH 8 by addition of aqueous sodium bicarbonate and then this mixture was extracted with ethyl acetate. The organic extracts were dried over magnesium sulfate and then evaporated to yield an oil. The crude product was subjected to flash column chromatography on silica eluting with ethyl acetate and 10% triethylamine to give 2-(1H-indazol-3-yl)-3H-benzoimidazol-5-amine (826 mg). MS: 250.31 (M+H)+. 248.31 (M−H)−. HPLC (Method B): RT=2.03 minutes.

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 16 hours
  3. extractionthis mixture was extracted with ethyl acetate
  4. dry with materialThe organic extracts were dried over magnesium sulfate
  5. customevaporated
  6. customto yield an oil

Sources & evidence

ORD record
ord-7afa539c30e24e4c9780f5caa932fff4
Source dataset
uspto-grants-2005_05
Patent number
US06897208B2

Reaction notes

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