Hydroxyamine hydrochloride → HCID 86591947, compound

HRID 1792025Notes

Reaction equation

HRID 1792025 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[N:22]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[CH:29]=O)[C:21]3[C:20](=[O:31])[N:19]([CH3:32])[C:18](=[O:33])[N:17]([CH3:34])[C:16]=3[N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[NH2:36][OH:37].C([O-])(=O)C.[K+]>C(O)C.O.C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([C:14]2[N:22]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[CH:29]=[N:36][OH:37])[C:21]3[C:20](=[O:31])[N:19]([CH3:32])[C:18](=[O:33])[N:17]([CH3:34])[C:16]=3[N:15]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:3])([CH3:2])[CH3:4]

Participants

7

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517044Potassium AcetateHCID 23081908HCID 23081908, compound

Product 1

HCID 86591947HCID 86591947, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-[7-(2-Formylphenyl)-1,3-dimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-yl]piperazine-1-carboxylic acid tert-butyl ester (13 mg) and hydroxylamine hydrochloride (10 mg) were dissolved in ethanol (1 ml) and water (0.2 ml), and potassium acetate (ca. 10 mg) was added thereto. The reaction solution was stirred for 0.5 hour at room temperature, diluted with ethyl acetate, and washed with sodium bicarbonate aqueous solution. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated under reduced pressure to give 4-[7-[2-(hydroxyiminomethyl)phenyl]-1,3-dimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-yl]piperazine-1-carboxylic acid tert-butyl ester. This was dissolved in dichloromethane (0.5 ml) and triethylamine (ca. 0.05 ml) and methanesulfonyl chloride (0.05 ml) were added thereto. The reaction mixture was stirred at room temperature for 0.5 hour, and the solvent was removed. The residue was dissolved in trifluoroacetic acid, and the solution was concentrated. The residue was purified by reversed phase high performance liquid chromatography to give 4.14 mg of the title compound.

Workup

  1. washwashed with sodium bicarbonate aqueous solution
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-905384ce403144c98d18bded1622e2ea
Source dataset
uspto-grants-2006_07
Patent number
US07074798B2

Reaction notes

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