Hydroxylamine, O-ethyl- → HCID 10266285, compound

HRID 1252701Notes

Reaction equation

HRID 1252701 reaction equation
[NH2:1][C:2]1[C:7]([C:8]([OH:10])=O)=[CH:6][N:5]=[C:4]2[N:11]([CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[N:12]=[CH:13][C:3]=12.[Cl-].C1(N(C2C=CC=CC=2)C([N+]2C=CC=CC=2)=O)C=CC=CC=1.[CH2:41]([O:43][NH2:44])[CH3:42].C[O-].[Na+].Cl.C(ON)C>CO.C(N(CC)CC)C>[NH2:1][C:2]1[C:7]([C:8]([NH:44][O:43][CH2:41][CH3:42])=[O:10])=[CH:6][N:5]=[C:4]2[N:11]([CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[N:12]=[CH:13][C:3]=12

Participants

8

Reactant 5

HCID 69357Hydroxylamine, O-ethyl-HCID 76850O-ethylhydroxylamine hydrochlorideHCID 10942334Sodium MethoxideHCID 12486269HCID 12486269, compoundHCID 145905404-Amino-1-pentyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid

Product 1

HCID 10266285HCID 10266285, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent3×HCID 8471TriethylamineSolvent

Procedure

To a stirred solution of 1.1 g of 4-amino-1-n-pentyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid and 0.56 g of triethylamine in 35 ml of MeOH was added a solution of 1.43 g of diphenylcarbamylpyridinium chloride in 5.6 ml of MeOH. After stirring for 20 min., the reaction mixture was cooled in an ice bath and added to a cold stirred solution of ethoxyamine which was prepared by adding 3.32 ml of a 25% methanolic sodium methoxide solution to a solution of 1.42 g of ethoxyamine hydrochloride in 10 ml of MeOH. The resulting mixture was stirred at room temperature for 1.5 hr. and then concentrated. The residue was diluted with 60 ml of water and the resulting mixture extracted with ether. The combined extracts were dried (MgSO4), filtered, and concentrated to give 1.98 g of an amber oil which was chromatographed over silica gel using ether as the eluant. The fractions containing the product were combined and concentrated to leave 0.92 g of a white foam. The foam was induced to crystallize by dissolving it in hot toluene containing a small amount of chloroform and cooling, whereupon crystals precipitated. These were collected, washed with cold toluene and hexane, and air-dried to give 0.69 g (53%) of the title compound as white crystals, m.p. 142.3°-144.2°.

Workup

  1. temperaturethe reaction mixture was cooled in an ice bath
  2. customwas prepared
  3. stirringThe resulting mixture was stirred at room temperature for 1.5 hr
  4. concentrationand then concentrated
  5. additionThe residue was diluted with 60 ml of water
  6. extractionthe resulting mixture extracted with ether
  7. dry with materialThe combined extracts were dried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-71fe41ca370c486cb77654b650a93401
Source dataset
uspto-grants-1988_05
Patent number
US04745121

Reaction notes

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