1,1-Dimethoxyethyl(dimethyl)amine → HCID 178465699, compound

HRID 2206860Notes

Reaction equation

HRID 2206860 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([CH2:8][O:9]/[N:10]=[C:11](/[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)\[C:12]2[N:16]([CH3:17])[C:15](=[O:18])[O:14][N:13]=2)[CH:5]=[CH:4][CH:3]=1.CO[C:27](OC)([N:29](C)C)[CH3:28].Cl.N[OH:36]>C(O)(C)C>[OH:36][N:29]=[C:27]([NH:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]([CH2:8][O:9]/[N:10]=[C:11](\[C:12]2[N:16]([CH3:17])[C:15](=[O:18])[O:14][N:13]=2)/[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:7]=1)[CH3:28]

Participants

5

Reactant 3

HCID 878351,1-Dimethoxyethyl(dimethyl)amineHCID 443297Hydroxyamine hydrochlorideHCID 894438773-[(E)-{[(6-aminopyridin-2-yl)methoxy]imino}(phenyl)methyl]-4-methyl-1,2,4-oxadiazol-5(4H)-one

Product 1

HCID 178465699HCID 178465699, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution of 3-[(Z)-{[(6-aminopyridin-2-yl)methoxy]imino}(phenyl)methyl]-4-methyl-1,2,4-oxadiazol-5(4H)-one (600 mg, 1.84 mol, 1 eq) in isopropanol (8 mL) was added N,N-dimethylacetamide dimethyl acetal. The mixture was refluxed for 4 h30. Hydroxylamine hydrochloride (154 mg, 2.21 mmol, 1.2 eq) was added at room temperature and the mixture was stirred at room temperature for 2 days. The solvent was then evaporated and water was added. The resulting precipitate was filtered and dried under vacuum to afford N′-hydroxy-N-{6-[({[(Z)-(4-methyl-5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}ethanimidamide (660 mg, 75% yield) as a white solid.

Workup

  1. temperatureThe mixture was refluxed for 4 h30
  2. customThe solvent was then evaporated
  3. additionwater was added
  4. filtrationThe resulting precipitate was filtered
  5. customdried under vacuum

Sources & evidence

ORD record
ord-4afa96bc819f48f2aa76efc2affbdbbf
Source dataset
uspto-grants-2016_06
Patent number
US09375010B2

Reaction notes

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