Ethanol → HCID 178513283, compound

HRID 1023865Notes

Reaction equation

HRID 1023865 reaction equation
Cl.[NH2:2][OH:3].C([O-])(O)=O.[Na+].C(O)C.[NH:12]1[CH:16]=[C:15]([C:17]2[CH:24]=[CH:23][CH:22]=[CH:21][C:18]=2[C:19]#[N:20])[N:14]=[CH:13]1>O.C1COCC1>[OH:3][NH:2][C:19](=[NH:20])[C:18]1[CH:21]=[CH:22][CH:23]=[CH:24][C:17]=1[C:15]1[N:14]=[CH:13][NH:12][CH:16]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 178509658HCID 178509658, compound

Product 1

HCID 178513283HCID 178513283, compoundYield 25%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

Hydroxylamine hydrochloride (56 mg, 0.804 mmol) was added to a solution of NaHCO3 (68 mg, 0.804 mmol) in water (0.5 mL). Ethanol (1.5 mL) was added followed by 2-(1H-imidazol-4-yl)benzonitrile in THF (0.5 mL) and the reaction mixture was heated at 80° C. for 18 h. Solvents were removed under reduced pressure and the remaining solution poured into water and extracted with EtOAc (2×20 mL). The combined organic layers were washed with brine (10 mL), dried, and concentrated. The residue was purified by flash column chromatography (silica gel, 5%-30% MeOH/DCM) to afford the desired product as a white solid (20 mg, 0.099 mmol, 25%). 1H NMR (DMSO-d6): 3.13 (s, 1H), 5.75 (s, 1H), 7.16-7.38 (m, 3H), 7.65 (s, 1H), 7.79 (s, 1H), 7.92 (d, 1H, J=7.6 Hz), 9.27 (s, 1H)

Workup

  1. customSolvents were removed under reduced pressure
  2. additionthe remaining solution poured into water
  3. extractionextracted with EtOAc (2×20 mL)
  4. washThe combined organic layers were washed with brine (10 mL)
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was purified by flash column chromatography (silica gel, 5%-30% MeOH/DCM)

Sources & evidence

ORD record
ord-1854d770e4204c41a4af7ef0cf4528e7
Source dataset
uspto-grants-2014_05
Patent number
US08722720B2

Reaction notes

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