Hydroxyamine hydrochloride → N-hydroxy-4-(6-methoxy-4-thiazol-2-yl-phthalazin-1-yl)-butyramide

HRID 2268915Notes

Reaction equation

HRID 2268915 reaction equation
[Na].Cl.[NH2:3][OH:4].C[O:6][C:7](=O)[CH2:8][CH2:9][CH2:10][C:11]1[C:20]2[C:15](=[CH:16][C:17]([O:21][CH3:22])=[CH:18][CH:19]=2)[C:14]([C:23]2[S:24][CH:25]=[CH:26][N:27]=2)=[N:13][N:12]=1>CO.O.[OH-].[Na+]>[OH:4][NH:3][C:7](=[O:6])[CH2:8][CH2:9][CH2:10][C:11]1[C:20]2[C:15](=[CH:16][C:17]([O:21][CH3:22])=[CH:18][CH:19]=2)[C:14]([C:23]2[S:24][CH:25]=[CH:26][N:27]=2)=[N:13][N:12]=1

Participants

7

Reactant 3

HCID 443297Hydroxyamine hydrochloride3×HCID 5360545Sodium3×HCID 543700044-(6-Methoxy-4-thiazol-2-yl-phthalazin-1-yl)-butyric acid methyl ester

Product 1

HCID 18381679N-hydroxy-4-(6-methoxy-4-thiazol-2-yl-phthalazin-1-yl)-butyramideYield 28.6%

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent2×HCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of sodium (388 mg, 16.9 mmoles) in CH3OH (6 ml) was added with hydroxylamine hydrochloride (1.3 g, 18.71 mmoles). The resultant solution was added to a solution of 4-(6-methoxy-4-thiazol-2-yl-phthalazin-1-yl)-butyric acid methyl ester (1.5 g, 4.4 mmoles), prepared as described in example 115, in CH3OH (30 ml), and stirred at room temperature for 2 days, then refluxed for 7 hours. NH2OH.HCl (1.6 g) and sodium (450 mg) were added, and the mixture was refluxed. After 1 night further NH2OH.HCl (0.9 g) and sodium (257 mg) were added, and the mixture was refluxed for 24 hours. The precipitate was filtered off and the mother liquors dried, taken up in water and filtered. The resultant solid was chromatographed (eluent: CH2Cl2/CH3OH 95:5) to give a solid which was suspended in water, dissolved in 10% NaOH and precipitated with saturated ammonium chloride to give 430 mg of the title compound (yield: 28.6%). m.p.: 189-190° C. (dec.).

Workup

  1. customprepared
  2. temperaturerefluxed for 7 hours
  3. temperaturethe mixture was refluxed
  4. temperaturethe mixture was refluxed for 24 hours
  5. filtrationThe precipitate was filtered off
  6. customthe mother liquors dried
  7. filtrationfiltered
  8. customThe resultant solid was chromatographed (eluent: CH2Cl2/CH3OH 95:5)
  9. customto give a solid which
  10. customprecipitated with saturated ammonium chloride

Sources & evidence

ORD record
ord-85d517ee015c43d7b2ecb5725dcde1ff
Source dataset
uspto-grants-2001_12
Patent number
US06329370B1

Reaction notes

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