Hydroxyamine hydrochloride → HCID 58442360, compound

HRID 444907Notes

Reaction equation

HRID 444907 reaction equation
[F:1][C:2]([F:29])([F:28])[CH:3]([OH:27])[CH2:4][NH:5][C:6]([C:8]1[C:13]([N:14]2C(C)=CC=C2C)=[CH:12][C:11]([C:21]([F:24])([F:23])[F:22])=[C:10]([O:25][CH3:26])[N:9]=1)=[O:7].Cl.NO>CCO.O>[F:29][C:2]([F:1])([F:28])[CH:3]([OH:27])[CH2:4][NH:5][C:6]([C:8]1[C:13]([NH2:14])=[CH:12][C:11]([C:21]([F:22])([F:24])[F:23])=[C:10]([O:25][CH3:26])[N:9]=1)=[O:7]

Participants

5

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 866576653-(2,5-Dimethyl-pyrrol-1-yl)-6-methoxy-5-trifluoromethyl-pyridine-2-carboxylic acid (3,3,3-trifluoro-2-hydroxy-propyl)-amide

Product 1

HCID 58442360HCID 58442360, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

3-(2,5-Dimethyl-pyrrol-1-yl)-6-methoxy-5-trifluoromethyl-pyridine-2-carboxylic acid (3,3,3-trifluoro-2-hydroxy-propyl)-amide (350 mg, 0.823 mmol) was dissolved in EtOH (14 ml) and water (7 ml). Hyroxylamine hydrochloride (572 mg, 8.23 mmol) was added followed by TEA (167 mg, 1.646 mmol) and the mixture was heated at reflux overnight. After cooling the RT, the mixture was purified by reverse phase chromatography eluting with MeOH; water (0.1% TFA) to afford the title compound as a pale yellow solid; LC-MS Rt=4.20 min [M+H]+ 348.2 (Method 10 minLC_v002)

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux overnight
  3. customthe mixture was purified by reverse phase chromatography
  4. washeluting with MeOH

Sources & evidence

ORD record
ord-00c41d37a8d04db7b22551bbb6977f32
Source dataset
uspto-grants-2013_07
Patent number
US08476269B2

Reaction notes

Loading…