Potassium Carbonate → 6-{5-[3-(Cyclopropylmethylamino)-pyridin-2-yl]-[1,2,4]oxadiazol-3-yl}-N-methyl-N-phenyl-[1,3,5]triazine-2,4-diamine

HRID 341461Notes

Reaction equation

HRID 341461 reaction equation
F[C:2]1[C:3]([C:8]2[O:12][N:11]=[C:10]([C:13]3[N:18]=[C:17]([N:19]([CH3:26])[C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[N:16]=[C:15]([NH2:27])[N:14]=3)[N:9]=2)=[N:4][CH:5]=[CH:6][CH:7]=1.[CH:28]1([CH2:31][NH2:32])[CH2:30][CH2:29]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C(Cl)Cl>[CH:28]1([CH2:31][NH:32][C:2]2[C:3]([C:8]3[O:12][N:11]=[C:10]([C:13]4[N:18]=[C:17]([N:19]([CH3:26])[C:20]5[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=5)[N:16]=[C:15]([NH2:27])[N:14]=4)[N:9]=3)=[N:4][CH:5]=[CH:6][CH:7]=2)[CH2:30][CH2:29]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 75646CyclopropanemethanamineHCID 569425726-[5-(3-Fluoropyridin-2-yl)-[1,2,4]oxadiazol-3-yl]-N-methyl-N-phenyl-[1,3,5]triazine-2,4-diamine

Product 1

HCID 668025676-{5-[3-(Cyclopropylmethylamino)-pyridin-2-yl]-[1,2,4]oxadiazol-3-yl}-N-methyl-N-phenyl-[1,3,5]triazine-2,4-diamineYield 44%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

6-[5-(3-Fluoropyridin-2-yl)-[1,2,4]oxadiazol-3-yl]-N-methyl-N-phenyl-[1,3,5]triazine-2,4-diamine (prepared in an analogous manner to Example 482, 50 mg, 0.137 mmol), 1-cyclopropylmethanamine (24 μL, 0.274 mmol) and potassium carbonate (57 mg, 0.411 mmol) were suspended in anhydrous DMF (2 mL) in a sealed tube at room temperature under nitrogen. The reaction mixture was stirred at 90 C for 3 h and then at 100 C for 18 h. The mixture was diluted with DCM (10 mL) and then washed with saturated aq. ammonium chloride (3×5 mL) and then brine (5 mL). The organic layer was dried over sodium sulfate and evaporated under vacuum. The crude residue was purified by flash chromatography (0-1% (7M ammonia in MeOH) in DCM) to afford the title compound (25 mg, 44%).

Workup

  1. waitat 100 C for 18 h
  2. washwashed with saturated aq. ammonium chloride (3×5 mL)
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. customevaporated under vacuum
  5. customThe crude residue was purified by flash chromatography (0-1% (7M ammonia in MeOH) in DCM)

Sources & evidence

ORD record
ord-c1ecd5cfb6494ebdad5a0f952cfbae33
Source dataset
uspto-grants-2014_11
Patent number
US08895733B2

Reaction notes

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