Hydroxyamine hydrochloride → HCID 71585443, compound

HRID 526311Notes

Reaction equation

HRID 526311 reaction equation
[CH3:1][N:2]1[CH2:25][CH2:24][N:5]2[C:6]3[CH:7]=[CH:8][CH:9]=[CH:10][C:11]=3[C:12]([S:13][C:14]3[CH:23]=[CH:22][C:17]([C:18](OC)=[O:19])=[CH:16][CH:15]=3)=[C:4]2[C:3]1=[O:26].[NH2:27][OH:28].Cl.C[O-].[Na+]>CO>[OH:28][NH:27][C:18](=[O:19])[C:17]1[CH:16]=[CH:15][C:14]([S:13][C:12]2[C:11]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=3[N:5]3[CH2:24][CH2:25][N:2]([CH3:1])[C:3](=[O:26])[C:4]=23)=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 10942334Sodium Methoxide2×HCID 89602064HCID 89602064, compound

Product 1

HCID 71585443HCID 71585443, compoundYield 38.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Procedure

To a solution of methyl 4-((2-methyl-1-oxo-1,2,3,4-tetrahydropyrazino[1,2-a]indol-10-yl)thio)benzoate (0.25 g, impure) and NH2OH.HCl (0.35 g) in 4 mL of dry MeOH was added 1.4 mL of 25% NaOMe solution in methanol. The reaction mixture was stirred for 20 min at r.t. and 0.3 mL of more 25% NaOMe solution in methanol was added. After stirring for 2 h, the reaction mixture was quenched with 10 mL of potassium phosphate buffer solution. The mixture was extracted with 2×30 mL of EtOAc. The combined extracts were dried over Na2SO4, filtered and concentrated. The residue was purified by silica gel chromatography eluted with up to 10% MeOH/CH2Cl2 to give 0.097 g of the title product as beige solid.

Workup

  1. stirringAfter stirring for 2 h
  2. customthe reaction mixture was quenched with 10 mL of potassium phosphate buffer solution
  3. extractionThe mixture was extracted with 2×30 mL of EtOAc
  4. dry with materialThe combined extracts were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography
  8. washeluted with up to 10% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-7936f437a3504f6d9dec5d40af11327c
Source dataset
uspto-grants-2016_05
Patent number
US09345905B2

Reaction notes

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