Isoamyl Nitrite → HCID 66614209, compound

HRID 510126Notes

Reaction equation

HRID 510126 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]([CH2:29][C:30]([CH3:33])([CH3:32])[CH3:31])[C:5](=[O:28])[NH:6]2.N(OCCC(C)C)=O.C(=O)([O-])O.[Na+]>O1CCCC1.[Cu](Cl)Cl>[CH3:31][C:30]([CH3:33])([CH3:32])[CH2:29][N:4]1[C:3]2[C:7](=[N:8][C:9]([C:11]3[C:19]4[C:14](=[N:15][CH:16]=[CH:17][CH:18]=4)[N:13]([CH2:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[F:27])[N:12]=3)=[N:10][CH:2]=2)[NH:6][C:5]1=[O:28]

Participants

6

Reactant 3

HCID 8053Isoamyl NitriteHCID 516892Sodium BicarbonateHCID 66614056HCID 66614056, compound

Product 1

HCID 66614209HCID 66614209, compound

Reagents, catalysts & solvents 2

HCID 24014Cupric ChlorideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

100 mg (0.22 mmol) of the compound from example 120 were initially charged in tetrahydrofuran (10 ml), then 0.21 ml (1.57 mmol) of isoamyl nitrite and 6.0 mg (0.05 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 34 mg (34% 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-82bc5bc5448e49a48e4155a6f5dc95d6
Source dataset
uspto-grants-2015_08
Patent number
US09096592B2

Reaction notes

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