Sodium Hydroxide → 5-(3-{4-Amino-6-[methyl(phenyl)amino]-1,3,5-triazin-2-yl}-1,2,4-oxadiazol-5-yl)pyridine-2-carboxylic acid

HRID 341494Notes

Reaction equation

HRID 341494 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([N:8]([CH3:15])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:5]=[C:4]([C:16]2[N:20]=[C:19]([C:21]3[CH:22]=[CH:23][C:24]([C:27]([O:29]C)=[O:28])=[N:25][CH:26]=3)[O:18][N:17]=2)[N:3]=1.[OH-].[Na+]>CO>[NH2:1][C:2]1[N:7]=[C:6]([N:8]([CH3:15])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:5]=[C:4]([C:16]2[N:20]=[C:19]([C:21]3[CH:22]=[CH:23][C:24]([C:27]([OH:29])=[O:28])=[N:25][CH:26]=3)[O:18][N:17]=2)[N:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66803428Methyl 5-(3-{4-amino-6-[methyl(phenyl)amino]-1,3,5-triazin-2-yl}-1,2,4-oxadiazol-5-yl)pyridine-2-carboxylate

Product 1

HCID 668034705-(3-{4-Amino-6-[methyl(phenyl)amino]-1,3,5-triazin-2-yl}-1,2,4-oxadiazol-5-yl)pyridine-2-carboxylic acidYield 87%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (methyl 5-(3-{4-amino-6-[methyl(phenyl)amino]-1,3,5-triazin-2-yl}-1,2,4-oxadiazol-5-yl)pyridine-2-carboxylate) (prepared in an analogous manner to Example 279, 500 mg, 1.23 mmol) in MeOH (20 mL) was added a 1M sodium hydroxide aq. solution (1.85 mL, 1.85 mmol). The solution was stirred at room temperature overnight and evaporated to dryness. The resulting solid was dissolved in water (20 mL) and the solution acidified to pH 3 with a 1M HCl aq. solution. The resulting solid was filtered and dried to afford the desired product as a beige solid (418 mg, 87%). Method C HPLC-MS: MH+ requires m/z=391. Found: m/z=390.9, Rt=1.16 min (95%).

Workup

  1. customevaporated to dryness
  2. dissolutionThe resulting solid was dissolved in water (20 mL)
  3. filtrationThe resulting solid was filtered
  4. customdried

Sources & evidence

ORD record
ord-37f4adc9945f4c4d9ab353ec884bd8c0
Source dataset
uspto-grants-2014_11
Patent number
US08895733B2

Reaction notes

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