O-Methylhydroxylamine hydrochloride → 1-Ethyl-3-[5-(1-methoxyimino-butyl)-7-pyridin-3-yl-[1,2,4]triazolo[1,5-a]pyridine-2-yl]-urea

HRID 2112956Notes

Reaction equation

HRID 2112956 reaction equation
[C:1]([C:6]1[N:11]2[N:12]=[C:13]([NH:15][C:16]([NH:18][CH2:19][CH3:20])=[O:17])[N:14]=[C:10]2[CH:9]=[C:8]([C:21]2[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=2)[CH:7]=1)(=O)[CH2:2][CH2:3][CH3:4].Cl.[CH3:28][O:29][NH2:30].O.O.O.C([O-])(=O)C.[Na+]>C(O)C>[CH2:19]([NH:18][C:16]([NH:15][C:13]1[N:14]=[C:10]2[CH:9]=[C:8]([C:21]3[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=3)[CH:7]=[C:6]([C:1](=[N:30][O:29][CH3:28])[CH2:2][CH2:3][CH3:4])[N:11]2[N:12]=1)=[O:17])[CH3:20]

Participants

5

Reactant 3

HCID 521874O-Methylhydroxylamine hydrochlorideHCID 23665404Sodium Acetate TrihydrateHCID 688353671-(5-Butyryl-7-pyridin-3-yl-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-3-ethyl-urea

Product 1

HCID 866180241-Ethyl-3-[5-(1-methoxyimino-butyl)-7-pyridin-3-yl-[1,2,4]triazolo[1,5-a]pyridine-2-yl]-urea

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-(5-Butyryl-7-pyridin-3-yl-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-3-ethyl-urea, which may be produced as in Example 108 (46.0 mg, 0.13 mmol) and O-methylhydroxylamine HCl (18.0 mg, 0.22 mmol) in ethanol (1.0 mL) were charged with sodium acetate trihydrate (55.0 mg, 0.41 mmol). After 24 h the reaction was concentrated then taken up in ethyl acetate and washed with saturated sodium bicarbonate. The organic was concentrated and the resulting oil chromatographed (0-10% isopropanol/CH2Cl2) to afford 1-ethyl-3-[5-(1-methoxyimino-butyl)-7-pyridin-3-yl-[1,2,4]triazolo[1,5-a]pyridine-2-yl]-urea. MS (APCI+): m/z 382.3 (M+H).

Workup

  1. concentrationAfter 24 h the reaction was concentrated
  2. washwashed with saturated sodium bicarbonate
  3. concentrationThe organic was concentrated
  4. customthe resulting oil chromatographed (0-10% isopropanol/CH2Cl2)

Sources & evidence

ORD record
ord-5d929ca115c74510b61de63a1cce2fc9
Source dataset
uspto-grants-2009_04
Patent number
US07524860B2

Reaction notes

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