Cyanogen Bromide → HCID 59467889, compound

HRID 1404951Notes

Reaction equation

HRID 1404951 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][CH2:11][C:12]([N:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH2:17][CH2:16][CH2:15]1)=[O:13].[N:24]#[C:25]Br.C([O-])([O-])=O.[K+].[K+]>CC#N.CCOC(C)=O>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[N:10]([CH2:11][C:12]([N:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH2:17][CH2:16][CH2:15]1)=[O:13])[C:25]#[N:24]

Participants

6

Reactant 3

HCID 10476Cyanogen Bromide2×HCID 11430Potassium CarbonateHCID 59467885HCID 59467885, compound

Product 1

HCID 59467889HCID 59467889, compoundYield 28%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of compound 83 (340 g, 1.05 mmol) in dry CH3CN (10 mL) were added cyanogen bromide (5M in CH3CN) (0.42 mL, 2.1 mmol) and K2CO3 (580 g, 4.2 mmol). The reaction was heated to reflux for 4 h under N2. 0.84 mL (4.2 mmol) of cyanogen bromide was added and the reflux was continued for 12 h. The reaction mixture was diluted with EtOAc (50 mL). The solids were filtered off, filtrate was concentrated, and the yellow residue was purified by column chromatography (20% EtOAc in hexanes) to afford 84 as an off-white solid (80 mg, 28%). MS m/z: 349 (M+H)+. Anal. Calcd. For, C19H16N4OS.0.6 H2O: C, 63.53; H, 4.83; N, 15.60; S, 8.92. Found: C, 63.24; H, 4.67; N, 15.25; S, 8.76.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 4 h under N2
  3. filtrationThe solids were filtered off
  4. concentrationfiltrate was concentrated
  5. customthe yellow residue was purified by column chromatography (20% EtOAc in hexanes)

Sources & evidence

ORD record
ord-d31cfa24692240f5a784ea94ad4a979b
Source dataset
uspto-grants-2014_12
Patent number
US08916550B2

Reaction notes

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