Hydroxyamine hydrochloride → HCID 71565457, compound

HRID 526299Notes

Reaction equation

HRID 526299 reaction equation
[CH3:1][N:2]1[CH2:25][CH2:24][C:5]2=[C:6]([S:13][C:14]3[CH:23]=[CH:22][C:17]([C:18](OC)=[O:19])=[CH:16][CH:15]=3)[C:7]3[C:12]([N:4]2[CH2:3]1)=[CH:11][CH:10]=[CH:9][CH:8]=3.[NH2:26][OH:27].Cl.C[O-].[Na+]>CO>[OH:27][NH:26][C:18](=[O:19])[C:17]1[CH:22]=[CH:23][C:14]([S:13][C:6]2[C:7]3[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=3)[N:4]3[CH2:3][N:2]([CH3:1])[CH2:25][CH2:24][C:5]=23)=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 10942334Sodium MethoxideHCID 89601745HCID 89601745, compound

Product 1

HCID 71565457HCID 71565457, compoundYield 29.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of methyl 4-((2-methyl-1,2,3,4-tetrahydropyrimido[1,6-a]indol-5-yl)thio)benzoate (0.4 g) and NH2OH.HCl (0.63 g) in 4 mL of dry MeOH was added 2.5 mL of 25% NaOMe solution in methanol. The reaction mixture was stirred for 4 h at r.t. and then quenched with 10 mL of potassium phosphate buffer solution. The mixture was extracted 40 mL of EtOAc. The extract was dried over Na2SO4, filtered and concentrated. The residue was purified by silica gel chromatography eluted with up to 10% MeOH/CH2Cl2 to give 0.12 g of the title product as white solid.

Workup

  1. customquenched with 10 mL of potassium phosphate buffer solution
  2. extractionThe mixture was extracted 40 mL of EtOAc
  3. dry with materialThe extract was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel chromatography
  7. washeluted with up to 10% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-a46e5846453b4fa2afd7a921a2b58ef3
Source dataset
uspto-grants-2016_05
Patent number
US09345905B2

Reaction notes

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