Potassium Cyanide → HCID 66802722, compound

HRID 341472Notes

Reaction equation

HRID 341472 reaction equation
Cl[C:2]1[N:7]=[C:6]([N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH2:10][CH2:9]2)[N:5]=[C:4]([NH2:17])[N:3]=1.[C-:18]#[N:19].[K+].C1OCCOCCOCCOCCOCCOC1>CN(C=O)C.CCOC(C)=O>[NH2:17][C:4]1[N:5]=[C:6]([N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH2:10][CH2:9]2)[N:7]=[C:2]([C:18]#[N:19])[N:3]=1

Participants

6

Reactant 3

HCID 9032Potassium CyanideHCID 2855718-Crown-6HCID 53410089HCID 53410089, compound2×

Product 1

HCID 66802722HCID 66802722, compoundYield 26.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-Chloro-6-(2,3-dihydro-indol-1-yl)-[1,3,5]triazin-2-ylamine (Intermediate 40, 680 mg, 2.48 mmol), potassium cyanide (323 mg, 4.96 mmol) and 18-crown-6 (328 mg, 1.24 mmol) were charged to a round-bottomed flask then taken up in DMF (12 mL). The resulting mixture was lowered into a heating block preheated to 110 C and stirred under nitrogen for 2 h and then at room temperature for 56 h. The reaction was then diluted with EtOAc (60 ml) and extracted with 5% aq. sodium carbonate solution (2×10 ml), brine (10 ml) and dried further over anhydrous magnesium sulfate. After evaporation of the solvent the crude residue was purified by FCC over silica gel eluting with heptane:EtOAc 1:0 to 8:2 to 1:1 to 0:1 and the column flushed with THF to give the title compound (155 mg, 26%). Method B HPLC-MS: MH+ requires m/z=239. Found: m/z=239, Rt=1.36 min (75%).

Workup

  1. waitat room temperature for 56 h
  2. extractionextracted with 5% aq. sodium carbonate solution (2×10 ml), brine (10 ml)
  3. dry with materialdried further over anhydrous magnesium sulfate
  4. customAfter evaporation of the solvent the crude residue
  5. customwas purified by FCC over silica gel eluting with heptane:EtOAc 1:0 to 8:2 to 1:1 to 0:1
  6. customthe column flushed with THF

Sources & evidence

ORD record
ord-8d57ce3d2f29481d87d10e073b826074
Source dataset
uspto-grants-2014_11
Patent number
US08895733B2

Reaction notes

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