6-Methoxy-3-pyridinylamine → 3-{4-Amino-6-[methyl(phenyl)amino]-1,3,5-triazin-2-yl}-N-(6-methoxypyridin-3-yl)-1,2,4-oxadiazole-5-carboxamide

HRID 341428Notes

Reaction equation

HRID 341428 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](OCC)=[O:22])[O:18][N:17]=2)[N:3]=1.C[Al](C)C.[CH3:30][O:31][C:32]1[N:37]=[CH:36][C:35]([NH2:38])=[CH:34][CH:33]=1>C1(C)C=CC=CC=1>[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]([NH:38][C:35]3[CH:36]=[N:37][C:32]([O:31][CH3:30])=[CH:33][CH:34]=3)=[O:22])[O:18][N:17]=2)[N:3]=1

Participants

5

Reactant 3

HCID 811216-Methoxy-3-pyridinylamineHCID 16682925TrimethylaluminumHCID 66803067Ethyl 3-{4-amino-6-[methyl(phenyl)amino]-1,3,5-triazin-2-yl}-1,2,4-oxadiazole-5-carboxylate

Product 1

HCID 668030643-{4-Amino-6-[methyl(phenyl)amino]-1,3,5-triazin-2-yl}-N-(6-methoxypyridin-3-yl)-1,2,4-oxadiazole-5-carboxamideYield 43%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of ethyl 3-{4-amino-6-[methyl(phenyl)amino]-1,3,5-triazin-2-yl}-1,2,4-oxadiazole-5-carboxylate (prepared in an analogous manner to Example 73, 0.2 g, 0.58 mmol) in toluene (10 mL) at 0 C was added trimethylaluminium (2M in toluene, 0.88 mL, 1.7 mmol) over a period of 5 min and the mixture was then stirred at room temperature for 2 h. 6-Methoxypyridin-3-amine (0.21 g, 1.7 mmol) was added and the mixture was heated to 60 C for 15 h. The mixture was cooled to room temperature and quenched with ice water. The mixture was extracted with EtOAc (3×20 mL) and the organic layers were concentrated under vacuum. The residue was slurried in acetonitrile for 30 min and the resultant precipitate was filtered off to afford the title compound (0.100 g, 43%).

Workup

  1. temperaturethe mixture was heated to 60 C for 15 h
  2. temperatureThe mixture was cooled to room temperature
  3. customquenched with ice water
  4. extractionThe mixture was extracted with EtOAc (3×20 mL)
  5. concentrationthe organic layers were concentrated under vacuum
  6. waitThe residue was slurried in acetonitrile for 30 min
  7. filtrationthe resultant precipitate was filtered off

Sources & evidence

ORD record
ord-9a645d08b3ea43299a9cd2587bcc1cd9
Source dataset
uspto-grants-2014_11
Patent number
US08895733B2

Reaction notes

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