Hydroxylamine → HCID 178526363, compound

HRID 1845761Notes

Reaction equation

HRID 1845761 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([C:12]2[C:16]([CH2:17][CH2:18][CH2:19][N:20]3[CH2:25][CH2:24][O:23][CH2:22][CH2:21]3)=[N:15][O:14][N:13]=2)=O)[CH:5]=[CH:6][C:7]=1[F:8].P(Cl)(Cl)(Cl)(Cl)Cl.[NH2:32][OH:33]>C1C=CC=CC=1.CCO.CO>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([C:12]2[C:16]([CH2:17][CH2:18][CH2:19][N:20]3[CH2:25][CH2:24][O:23][CH2:22][CH2:21]3)=[N:15][O:14][N:13]=2)=[N:32][OH:33])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

7

Reactant 3

HCID 787HydroxylamineHCID 24819Phosphorus pentachlorideHCID 58941763N-(3-chloro-4-fluorophenyl)-4-(3-morpholin-4-ylpropyl)-1,2,5-oxadiazole-3-carboxamide

Product 1

HCID 178526363HCID 178526363, compoundYield 50%

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

N-(3-Chloro-4-fluorophenyl)-4-(3-morpholin-4-ylpropyl)-1,2,5-oxadiazole-3-carboxamide (10.0 mg, 27.1 μmol) was suspended in benzene (0.4 mL) under a nitrogen atmosphere and phosphorus pentachloride (6.2 mg, 29.8 μmol) was added and the solution was heated at reflux for 2.5 h. The reaction was then stripped to dryness in vacuo. The reaction was dissolved in EtOH (0.3 mL) and hydroxylamine (40 μL, 0.7 mmol) (50% solution in water) was added to the reaction. After stirring for 1 h, the reaction solution was diluted with MeOH and purified with preparative LCMS to give product (5.2 mg, 50%). LCMS for C16H20ClFN5O3(M+H)+: m/z=384.1.

Workup

  1. temperaturethe solution was heated
  2. temperatureat reflux for 2.5 h
  3. custompurified with preparative LCMS

Sources & evidence

ORD record
ord-27cf08080ca245c785f5d858aff0fa4e
Source dataset
uspto-grants-2015_02
Patent number
US08951536B2

Reaction notes

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