Potassium Sodium Tartrate → 2-(3-Ethyl-ureido)-7-pyridin-3-yl-[1,2,4]triazolo[1,5-a]pyridine-5-carboxylic acid methoxy-methyl-amide

HRID 2112954Notes

Reaction equation

HRID 2112954 reaction equation
Cl.[CH3:2][N:3](C)[OH:4].C[Al](C)C.C(O[C:13]([C:15]1[N:20]2[N:21]=[C:22]([NH:24][C:25]([NH:27][CH2:28][CH3:29])=[O:26])[N:23]=[C:19]2[CH:18]=[C:17]([C:30]2[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=2)[CH:16]=1)=[O:14])C.[C@H:36](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>C1COCC1.C(OCC)(=O)C>[CH3:36][O:4][N:3]([CH3:2])[C:13]([C:15]1[N:20]2[N:21]=[C:22]([NH:24][C:25]([NH:27][CH2:28][CH3:29])=[O:26])[N:23]=[C:19]2[CH:18]=[C:17]([C:30]2[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=2)[CH:16]=1)=[O:14]

Participants

7

Reactant 4

HCID 9357Potassium Sodium TartrateHCID 27969N,N-dimethylhydroxylamine hydrochlorideHCID 16682925TrimethylaluminumHCID 576431092-(3-Ethyl-ureido)-7-pyridin-3-yl-[1,2,4]triazolo[1,5-a]pyridine-5-carboxylic acid ethyl ester

Product 1

HCID 866180232-(3-Ethyl-ureido)-7-pyridin-3-yl-[1,2,4]triazolo[1,5-a]pyridine-5-carboxylic acid methoxy-methyl-amide

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Dimethylhydroxylamine HCl salt (1.40 g, 14.5 mmol) in THF (15.0 mL) was cooled to 0° C. and treated with trimethylaluminum (1.80 mL). After 1 h the solution was charged with 2-(3-ethyl-ureido)-7-pyridin-3-yl-[1,2,4]triazolo[1,5-a]pyridine-5-carboxylic acid ethyl ester (which may be produced as in Example 16, Step 1) (1.01 g, 2.84 mmol). After 20 h the reaction was diluted in ethyl acetate and charged with an equal amount of Rochelle salt. This biphasic solution was stirred rapidly for 4 h. then separated and the organic dried over magnesium sulfate and concentrated to afford 2-(3-ethyl-ureido)-7-pyridin-3-yl-[1,2,4]triazolo[1,5-a]pyridine-5-carboxylic acid methoxy-methyl-amide. MS (APCI+): m/z 370.4 (M+H).

Workup

  1. customthen separated
  2. dry with materialthe organic dried over magnesium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-830ee3402145446ba3df89dc54fb4938
Source dataset
uspto-grants-2009_04
Patent number
US07524860B2

Reaction notes

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