Hydroxyamine hydrochloride → HCID 86650132, compound

HRID 2197503Notes

Reaction equation

HRID 2197503 reaction equation
[F:1][C:2]([F:21])([F:20])[C:3](=O)[CH2:4][C:5]([C:7]1[C:16](=[O:17])[NH:15][C:10]2=[N:11][CH:12]=[CH:13][N:14]=[C:9]2[C:8]=1[OH:18])=[O:6].Cl.[NH2:23][OH:24]>C(O)C>[F:1][C:2]([F:21])([F:20])[C:3](=[N:23][OH:24])[CH2:4][C:5]([C:7]1[C:16](=[O:17])[NH:15][C:10]2=[N:11][CH:12]=[CH:13][N:14]=[C:9]2[C:8]=1[OH:18])=[O:6]

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 66851243HCID 66851243, compound

Product 1

HCID 86650132HCID 86650132, compoundYield 43.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 4,4,4-trifluoro-1-(8-hydroxy-6-oxo-5,6-dihydro-pyrido[2,3-b]pyrazin-7-yl)-butane-1,3-dione (Example 6.3) (0.170 g) in ethanol (2 ml) was added hydroxylamine hydrochloride (0.050 g). The reaction mixture was heated to reflux for 4 hours and was then stored at ambient temperature for 16 hours. The solid was isolated by filtration and washed with ethanol, ethyl acetate, and diethyl ether and dried to give 4,4,4-trifluoro-1-(8-hydroxy-6-oxo-5,6-dihydro-pyrido[2,3-b]pyrazin-7-yl)-butane-1,3-dione 3-oxime as a brown solid (0.078 g). 1H-NMR (400 MHz, d6-DMSO): 3.61 (d, 1H), 3.86 (d, 1H), 8.57 (d, 1H), 8.67 (d, 1H), 12.35 (s, 1H) ppm.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 4 hours
  3. customThe solid was isolated by filtration
  4. washwashed with ethanol, ethyl acetate, and diethyl ether
  5. customdried

Sources & evidence

ORD record
ord-294083d959e04c37ac100002d1d8c53a
Source dataset
uspto-grants-2012_12
Patent number
US08338598B2

Reaction notes

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