Triethylamine → HCID 136047358, compound

HRID 410018Notes

Reaction equation

HRID 410018 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:24])[C:7]([C:16]3[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[CH:18][CH:17]=3)=[C:8]([C:12]([F:15])([F:14])[F:13])[O:9]2)=[CH:4][CH:3]=1.Cl.N[OH:27].C(N(CC)CC)C.C1N=CN([C:40]([N:42]2C=NC=C2)=[O:41])C=1>C(O)C>[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:24])[C:7]([C:16]3[CH:23]=[CH:22][C:19]([C:20]4[NH:42][C:40](=[O:27])[O:41][N:21]=4)=[CH:18][CH:17]=3)=[C:8]([C:12]([F:15])([F:13])[F:14])[O:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 443297Hydroxyamine hydrochlorideHCID 67366080HCID 67366080, compound

Product 1

HCID 136047358HCID 136047358, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4-(7-hydroxy-4-oxo-2-(trifluoromethyl)-4H-chromen-3-yl)benzonitrile (see Example 1, step 1 for synthesis) (200 mg, 0.60 mmol) and hydroxylamine hydrochloride (218 mg, 3.13 mmol) in absolute ethanol (2 ml) was added dropwise triethylamine (0.7 ml). The resulting mixture was heated to reflux for 5 hours. The volatiles were evaporated and the residue was dissolved in anhydrous THF (2 ml). CDI (296 mg, 1.83 mmol) was added and the suspension was heated to reflux overnight. The volatiles were evaporated and the residue was purified by prep-TLC (pure EtOAc) and prep-HPLC to afford desired product in Example 9 (35 mg, 15%) as a white solid.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux for 5 hours
  3. customThe volatiles were evaporated
  4. dissolutionthe residue was dissolved in anhydrous THF (2 ml)
  5. temperaturethe suspension was heated
  6. temperatureto reflux overnight
  7. customThe volatiles were evaporated
  8. customthe residue was purified by prep-TLC (pure EtOAc)

Sources & evidence

ORD record
ord-d3bbb1ab58f7465b90643546a0baddde
Source dataset
uspto-grants-2014_06
Patent number
US08759548B2

Reaction notes

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