Cesium carbonate → 2-{[5-(3-{4-Amino-6-[methyl(phenyl)amino]-1,3,5-triazin-2-yl}-1,2,4-oxadiazol-5-yl)pyridin-2-yl]oxy}acetonitrile

HRID 341443Notes

Reaction equation

HRID 341443 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]([OH:27])=[N:25][CH:26]=3)[O:18][N:17]=2)[N:3]=1.I[CH2:29][C:30]#[N:31].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.O>[NH2:1][C:2]1[N:7]=[C:6]([N:8]([CH3:15])[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:5]=[C:4]([C:16]2[N:20]=[C:19]([C:21]3[CH:22]=[CH:23][C:24]([O:27][CH2:29][C:30]#[N:31])=[N:25][CH:26]=3)[O:18][N:17]=2)[N:3]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 69356Iodoacetonitrile2×HCID 178482120HCID 178482120, compound2×

Product 1

HCID 569419822-{[5-(3-{4-Amino-6-[methyl(phenyl)amino]-1,3,5-triazin-2-yl}-1,2,4-oxadiazol-5-yl)pyridin-2-yl]oxy}acetonitrileYield 2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 5-(3-{4-amino-6-[methyl(phenyl)amino]-1,3,5-triazin-2-yl}-1,2,4-oxadiazol-5-yl)pyridin-2-ol (Intermediate 136, 0.150 g, 0.414 mmol), 2-iodoacetonitrile (0.036 mL, 0.497 mmol), cesium carbonate (0.270 g, 0.827 mmol) in DMF (2 mL) was stirred at 90 C in a pressure tube for 18 h. A further 0.6 equivalent of 2-iodoacetonitrile was added and the mixture was stirred overnight at 90 C. The reaction mixture was cooled to room temperature, diluted with water, the precipitate was collected by filtration, washed with water and dried under vacuum. The resulting solid was purified by preparative HPLC to afford the title compound (3 mg, 2%).

Workup

  1. stirringthe mixture was stirred overnight at 90 C
  2. filtrationthe precipitate was collected by filtration
  3. washwashed with water
  4. customdried under vacuum
  5. customThe resulting solid was purified by preparative HPLC

Sources & evidence

ORD record
ord-4225f296082d4bbf92a9d5ab08127e04
Source dataset
uspto-grants-2014_11
Patent number
US08895733B2

Reaction notes

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