Isoamyl Nitrite → HCID 66614229, compound

HRID 510128Notes

Reaction equation

HRID 510128 reaction equation
N[C:2]1[N:10]=[C:9]([C:11]2[C:19]3[C:14](=[N:15][CH:16]=[CH:17][CH:18]=3)[N:13]([CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[F:27])[N:12]=2)[N:8]=[C:7]2[C:3]=1[N:4]([CH:29]1[CH2:32][CH2:31][CH2:30]1)[C:5](=[O:28])[NH:6]2.N(OCCC(C)C)=O.C(=O)([O-])O.[Na+]>O1CCCC1.[Cu](Cl)Cl>[CH:29]1([N:4]2[C:3]3[C:7](=[N:8][C:9]([C:11]4[C:19]5[C:14](=[N:15][CH:16]=[CH:17][CH:18]=5)[N:13]([CH2:20][C:21]5[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=5[F:27])[N:12]=4)=[N:10][CH:2]=3)[NH:6][C:5]2=[O:28])[CH2:32][CH2:31][CH2:30]1

Participants

6

Reactant 3

HCID 8053Isoamyl NitriteHCID 516892Sodium BicarbonateHCID 66614413HCID 66614413, compound

Product 1

HCID 66614229HCID 66614229, compound

Reagents, catalysts & solvents 2

HCID 24014Cupric ChlorideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

50 mg (0.12 mmol) of the compound from example 121 were initially charged in tetrahydrofuran (5 ml), then 0.11 ml (0.81 mmol) of isoamyl nitrite and 3 mg (0.02 mmol) of copper(II) chloride were added, and the mixture was stirred at RT overnight. The reaction mixture was admixed with saturated aqueous sodium hydrogencarbonate solution and extracted twice with ethyl acetate. The collected organic phases were dried over sodium sulfate, filtered and concentrated. The residue was purified by means of preparative HPLC (eluent: acetonitrile/water with 0.1% formic acid gradient). This gave 7 mg (13% of theory) of the title compound in solid form.

Workup

  1. extractionextracted twice with ethyl acetate
  2. dry with materialThe collected organic phases were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by means of preparative HPLC (eluent: acetonitrile/water with 0.1% formic acid gradient)

Sources & evidence

ORD record
ord-7457b7e8e342406a9c448a056209ddae
Source dataset
uspto-grants-2015_08
Patent number
US09096592B2

Reaction notes

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