Hydroxyamine hydrochloride → HCID 178513266, compound

HRID 1241519Notes

Reaction equation

HRID 1241519 reaction equation
[N:1]1([CH2:6][CH:7]2[CH2:10][CH:9]([C:11]3[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][CH:12]=3)[CH2:8]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C([O-])(O)=O.[Na+].Cl.[NH2:25][OH:26]>CO>[N:1]1([CH2:6][CH:7]2[CH2:10][CH:9]([C:11]3[CH:12]=[CH:13][C:14]([C:15]([NH:25][OH:26])=[NH:16])=[CH:17][CH:18]=3)[CH2:8]2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 11459111HCID 11459111, compound

Product 1

HCID 178513266HCID 178513266, compoundYield 29.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

To a stirring solution of Example 222 (4-(3-Pyrrolidin-1-ylmethyl-cyclobutyl)-benzonitrile) (150 mg, 0.62 mmol) in MeOH (1.5 mL) was added NaHCO3 (58 mg, 0.62 mmol), followed by hydroxylamine hydrochloride (43.4 mg, 0.62 mmol). The reaction was then heated to 70° C. over night. Both TLC and MS analysis indicated complete consumption of starting material. The reaction was cooled to room temperature and concentrated under reduced pressure. Water was added and a gummy solid formed. The water was removed and the residual was taken up in MeOH and concentrated under reduced pressure to yield the title compound (50 mg, 29% yield). This material was used without further purification.

Workup

  1. customconsumption of starting material
  2. temperatureThe reaction was cooled to room temperature
  3. concentrationconcentrated under reduced pressure
  4. additionWater was added
  5. customa gummy solid formed
  6. customThe water was removed
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a5b9f5ecbc65488993692f8c20df42d3
Source dataset
uspto-grants-2006_10
Patent number
US07115600B2

Reaction notes

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