Hydroxylamine → HCID 178526363, compound

HRID 1845790Notes

Reaction equation

HRID 1845790 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.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

6

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 50.2%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 887MethanolSolvent

Procedure

N-(3-Chloro-4-fluorophenyl)-4-(3-morpholin-4-ylpropyl)-1,2,5-oxadiazole-3-carboxamide (10.0 mg, 27 μmol) was suspended in benzene (0.4 mL) under an atmosphere of nitrogen and phosphorus pentachloride (6.2 mg, 29.8 μmol) was added. The solution was heated at reflux for 2.5 h. The volatiles were evaporated 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 by preparative LCMS to give the desired 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. customThe volatiles were evaporated in vacuo
  4. dissolutionThe reaction was dissolved in EtOH (0.3 mL)
  5. custompurified by preparative LCMS

Sources & evidence

ORD record
ord-0272e5ff2f7f4a51883797f1838c9550
Source dataset
uspto-grants-2015_02
Patent number
US08951536B2

Reaction notes

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