Isoamyl Nitrite → HCID 86653846, compound

HRID 508175Notes

Reaction equation

HRID 508175 reaction equation
N[C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][OH:19])=[C:12]([F:20])[CH:11]=2)[C:5]([C:21]#[N:22])=[C:4]([S:23][CH2:24][C:25]2[N:26]=[C:27]([C:30]3[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=3)[O:28][CH:29]=2)[N:3]=1.N(OCCC(C)C)=O.[Cl-:45].[NH4+]>C(#N)C.[Cu](Cl)Cl>[Cl:45][C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][OH:19])=[C:12]([F:20])[CH:11]=2)[C:5]([C:21]#[N:22])=[C:4]([S:23][CH2:24][C:25]2[N:26]=[C:27]([C:30]3[CH:31]=[CH:32][C:33]([Cl:36])=[CH:34][CH:35]=3)[O:28][CH:29]=2)[N:3]=1

Participants

6

Reactant 3

HCID 8053Isoamyl NitriteHCID 25517Ammonium ChlorideHCID 67215914HCID 67215914, compound

Product 1

HCID 86653846HCID 86653846, compound

Reagents, catalysts & solvents 2

HCID 24014Cupric ChlorideCatalystHCID 6342AcetonitrileSolvent

Procedure

150 mg (0.287 mmol) of 2-amino-6-({[2-(4-chlorophenyl)-1,3-oxazol-4-yl]methyl}sulfanyl)-4-[3-fluoro-4-(2-hydroxyethoxy)phenyl]pyridine-3,5-dicarbonitrile (Example 20) are initially charged in 20 ml of acetonitrile, 258 μl (1.724 mmol) of isoamyl nitrite and 232 mg (1.724 mmol) of copper(II) chloride are added and the mixture is stirred at room temperature overnight. The reaction mixture is then added to saturated ammonium chloride solution and extracted with ethyl acetate. The organic phase is washed with saturated sodium chloride solution, dried over sodium sulfate and concentrated. The residue is purified by preparative HPLC (mobile phase gradient: acetonitrile/water 10:90→95:5). This gives 25 mg (16% of theory) of the target compound.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic phase is washed with saturated sodium chloride solution
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customThe residue is purified by preparative HPLC (mobile phase gradient: acetonitrile/water 10:90→95:5)

Sources & evidence

ORD record
ord-f2fde6f7f2c5490e8f44eed71d10c6ca
Source dataset
uspto-grants-2015_08
Patent number
US09095582B2

Reaction notes

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