Dimethylformamide → 5-(3-{4-Amino-6-[methyl(phenyl)amino]-1,3,5-triazin-2-yl}-1,2,4-oxadiazol-5-yl)pyridine-2-carboxamide

HRID 341431Notes

Reaction equation

HRID 341431 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)=[O:28])=[N:25][CH:26]=3)[O:18][N:17]=2)[N:3]=1.C(Cl)(=O)C(Cl)=O.C[N:37](C=O)C>ClCCCl.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]([NH2:37])=[O:28])=[N:25][CH:26]=3)[O:18][N:17]=2)[N:3]=1

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 668034705-(3-{4-Amino-6-[methyl(phenyl)amino]-1,3,5-triazin-2-yl}-1,2,4-oxadiazol-5-yl)pyridine-2-carboxylic acid2×

Product 1

HCID 668030815-(3-{4-Amino-6-[methyl(phenyl)amino]-1,3,5-triazin-2-yl}-1,2,4-oxadiazol-5-yl)pyridine-2-carboxamideYield 30%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 887MethanolSolvent

Procedure

To a solution of 5-(3-{4-amino-6-[methyl(phenyl)amino]-1,3,5-triazin-2-yl}-1,2,4-oxadiazol-5-yl)pyridine-2-carboxylic acid (Intermediate 124, 50 mg, 128 μmol) in DCE (10 mL) and DMF (100 μL) was added oxalyl chloride (22 μL, 256 μmol). The resulting solution was stirred at room temperature for 2 h, evaporated to dryness and re-suspended in a solution of ammonia in dioxane (7N, 10 mL). The reaction mixture was stirred overnight at room temperature and then poured into water (50 mL). The mixture was extracted with DCM (3×50 mL) and the combined organics were dried and concentrated under vacuum to afford a crude yellow solid. The crude material was suspended in MeOH, filtered and washed with further MeOH. The resulting solid was recrystallised in dioxane and water to afford the title compound as a white solid (15 mg, 30%).

Workup

  1. customevaporated to dryness
  2. stirringThe reaction mixture was stirred overnight at room temperature
  3. additionpoured into water (50 mL)
  4. extractionThe mixture was extracted with DCM (3×50 mL)
  5. customthe combined organics were dried
  6. concentrationconcentrated under vacuum
  7. customto afford a crude yellow solid
  8. filtrationfiltered
  9. washwashed with further MeOH
  10. customThe resulting solid was recrystallised in dioxane

Sources & evidence

ORD record
ord-ccf8fc889d774f8b9705f79f65b1f591
Source dataset
uspto-grants-2014_11
Patent number
US08895733B2

Reaction notes

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