Hydroxyamine hydrochloride → HCID 178463012, compound

HRID 490913Notes

Reaction equation

HRID 490913 reaction equation
[CH2:1]([N:3]1[C:7]2=[N:8][CH:9]=[C:10]([C:19]#[N:20])[C:11]([NH:12][CH:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)=[C:6]2[CH:5]=[N:4]1)[CH3:2].Cl.[NH2:22][OH:23].C(=O)([O-])O.[Na+]>CCO>[CH2:1]([N:3]1[C:7]2=[N:8][CH:9]=[C:10]([C:19](=[NH:20])[NH:22][OH:23])[C:11]([NH:12][CH:13]3[CH2:14][CH2:15][O:16][CH2:17][CH2:18]3)=[C:6]2[CH:5]=[N:4]1)[CH3:2]

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 57675218HCID 57675218, compound

Product 1

HCID 178463012HCID 178463012, compoundYield 41.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Intermediate 137 (3.50 g, 12.9 mmol), hydroxylamine hydrochloride (3.30 g, 47.8 mmol) and sodium hydrogencarbonate (4.01 g, 47.8 mmol) in EtOH (45 ml) were heated at 45° C. for 1.5 hours then at 50° C. for 2.5 hours. The suspension was concentrated in vacuo and the solid stirred in dichloromethane (80 ml) for 0.5 hours. The mixture was filtered and the solid stirred in EtOH, the resultant mixture was filtered and the filtrate evaporated. The solid was then washed with dichloromethane three time to afford Intermediate 138 as a white solid (1.62 g). LCMS showed MH+=305; TRET=1.85 min

Workup

  1. concentrationThe suspension was concentrated in vacuo
  2. filtrationThe mixture was filtered
  3. stirringthe solid stirred in EtOH
  4. filtrationthe resultant mixture was filtered
  5. customthe filtrate evaporated
  6. washThe solid was then washed with dichloromethane three time

Sources & evidence

ORD record
ord-4a640a82d17f4790b5842ee39c8cd7ee
Source dataset
uspto-grants-2009_05
Patent number
US07528148B2

Reaction notes

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