Triethylamine → HCID 59133019, compound

HRID 643356Notes

Reaction equation

HRID 643356 reaction equation
[NH:1]1[CH:5]=[N:4][CH:3]=[N:2]1.P(Cl)(Cl)(Cl)=O.C(N(CC)CC)C.[CH:18]1([C:24]2[N:32]3[C:27](C(=O)NC=N3)=[C:26]([I:34])[N:25]=2)[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1>C(#N)C>[CH:18]1([C:24]2[N:32]3[C:27]([C:5]([NH2:1])=[N:4][CH:3]=[N:2]3)=[C:26]([I:34])[N:25]=2)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 92571H-1,2,4-TriazoleHCID 24813Phosphorus oxychlorideHCID 136102521HCID 136102521, compound

Product 1

HCID 59133019HCID 59133019, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of 1H-1,2,4-triazole (1 g, 0.02 mol) in acetonitrile (23 mL) was added dropwise phosphoryl chloride (0.6 mL, 0.007 mol) and triethylamine (3 mL, 0.02 mol) at 0° C. To this mixture was added 7-cyclohexyl-5-iodoimidazo[5,1-f][1,2,4]triazin-4(3H)-one (77 mg, 0.224 mmol) and the resulting mixture refluxed overnight. The cooled mixture was then quenched with excess NH3 in iPrOH (pH 8) stirred at rt for 30 min. then filtered and the isolated solid washed with DCM. The filtrate was concentrated in vacuo and purified by chromatography over silica gel eluting with 2% MeOH in DCM to afford the 7-cyclohexyl-5-iodoimidazo[5,1-f][1,2,4]triazin-4-amine. 1H NMR (400 MHz-DMSO-d6) δ 1.14-1.91 (m, 10H), 3.11-3.18 (m, 1H), 6.75 (br.s, 1H), 7.84 (s, 1H) 8.42 (bs, 1H); MS (ES+): m/z: 344.01 (100) [MH+]. HPLC: tR=3.10 min (OpenLynx: polar—5 min).

Workup

  1. temperaturethe resulting mixture refluxed overnight
  2. customThe cooled mixture was then quenched with excess NH3 in iPrOH (pH 8)
  3. filtrationthen filtered
  4. washthe isolated solid washed with DCM
  5. concentrationThe filtrate was concentrated in vacuo
  6. custompurified by chromatography over silica gel eluting with 2% MeOH in DCM

Sources & evidence

ORD record
ord-b6e454a737a34a7999cba9055ab57f96
Source dataset
uspto-grants-2010_04
Patent number
US07700594B2

Reaction notes

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