Sodium Cyanide → HCID 67453473, compound

HRID 2276764Notes

Reaction equation

HRID 2276764 reaction equation
[C-:1]#[N:2].[Na+].Cl[C:5]1[CH:6]=[C:7]([C:11]2[N:12]=[N:13][C:14]([NH:17][CH2:18][C:19]([C:22]3[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=3)([CH3:21])[CH3:20])=[CH:15][N:16]=2)[CH:8]=[CH:9][CH:10]=1>CN1C(=O)CCC1>[F:28][C:25]1[CH:26]=[CH:27][C:22]([C:19]([CH3:21])([CH3:20])[CH2:18][NH:17][C:14]2[N:13]=[N:12][C:11]([C:7]3[CH:6]=[C:5]([CH:10]=[CH:9][CH:8]=3)[C:1]#[N:2])=[N:16][CH:15]=2)=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 67453355HCID 67453355, compound

Product 1

HCID 67453473HCID 67453473, compoundYield 48.7%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
200 °C

Procedure

To a microwave vial containing NiBr2 (280 mg, 1.3 mmol) and NaCN (120 mg, 2.5 mmol) was added a solution of 3-(3-chlorophenyl)-N-(2-(4-fluorophenyl)-2-methylpropyl)-1,2,4-triazin-6-amine (450 mg, 1.3 mmol) in NMP (4.0 mL). The vial was purged with nitrogen and sealed. The mixture was heated to 200° C. in a microwave for 25 min and allowed to cool to room temperature. The solution was diluted with EtOAc/ether (1:1), washed with water (3×), dried over Na2SO4 and evaporated to dryness. Purification using silica gel chromatography (0-65% EtOAc/hexanes) gave the desired product (220 mg) as an off white foam.

Workup

  1. customThe vial was purged with nitrogen
  2. customsealed
  3. temperatureto cool to room temperature
  4. additionThe solution was diluted with EtOAc/ether (1:1)
  5. washwashed with water (3×)
  6. dry with materialdried over Na2SO4
  7. customevaporated to dryness
  8. customPurification

Sources & evidence

ORD record
ord-5188039a3dd44723b531fec2c1488829
Source dataset
uspto-grants-2015_09
Patent number
US09133123B2

Reaction notes

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