Hydrochloric Acid → HCID 76384212, compound

HRID 2040882Notes

Reaction equation

HRID 2040882 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]#[C:9][C:10]2[CH2:14][C:13]3([C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[C:16](=O)[CH2:15]3)[O:12][N:11]=2)[CH:5]=[CH:6][CH:7]=1.[CH3:24][O:25][NH2:26].Cl>N1C=CC=CC=1.O>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]#[C:9][C:10]2[CH2:14][C:13]3([C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[C:16](=[N:26][O:25][CH3:24])[CH2:15]3)[O:12][N:11]=2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 4113O-MethylhydroxylamineHCID 56644431HCID 56644431, compound

Product 1

HCID 76384212HCID 76384212, compoundYield 75.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

To a solution of the Compound of Example 83 (0.14 g, 0.44 mmol) in 1.5 mL of pyridine was added O-methylhydroxylamine (0.04 g, 0.48 mmol). After 4 hours stirring at r.t., the reaction was checked by TLC and considered to completion. It was diluted with water, acidified by 1N HCl and extracted with EtOAc. After drying on Na2SO4 and evaporation to dryness, the residue from evaporation was purified by means of automated flash chromatography (SP01®TM-Biotage; gradient Petroleum Ether-EtOAc from 95:5 to 1:1) to give the title compound as a colorless oil. Yield: 75.4%

Workup

  1. extractionextracted with EtOAc
  2. customAfter drying on Na2SO4 and evaporation to dryness
  3. customthe residue from evaporation
  4. customwas purified by means of automated flash chromatography (SP01®TM-Biotage; gradient Petroleum Ether-EtOAc from 95:5 to 1:1)

Sources & evidence

ORD record
ord-30ad91b5047b4b01b5c0ce418ac01d5f
Source dataset
uspto-grants-2013_11
Patent number
US08580962B2

Reaction notes

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