Pyridine → N-{3-[2-amino-6-(2-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-3-cyano-4-pyridinyl]phenyl}-5-oxotetrahydro-2-furancarboxamide

HRID 2218248Notes

Reaction equation

HRID 2218248 reaction equation
N1C=CC=CC=1.[NH2:7][C:8]1[N:15]=[C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[O:22][Si:23]([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24])[CH:13]=[C:12]([C:30]2[CH:35]=[CH:34][CH:33]=[C:32]([NH2:36])[CH:31]=2)[C:9]=1[C:10]#[N:11].C1COCC1.[O:42]=[C:43]1[O:47][CH:46]([C:48](Cl)=[O:49])[CH2:45][CH2:44]1>C(#N)C>[NH2:7][C:8]1[C:9]([C:10]#[N:11])=[C:12]([C:30]2[CH:31]=[C:32]([NH:36][C:48]([CH:46]3[CH2:45][CH2:44][C:43](=[O:42])[O:47]3)=[O:49])[CH:33]=[CH:34][CH:35]=2)[CH:13]=[C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[O:22][Si:23]([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:24])[CH3:25])[N:15]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 8028TetrahydrofuranHCID 108445405-Oxotetrahydro-2-furancarbonyl chlorideHCID 597696742-Amino-4-(3-aminophenyl)-6-(2-{[tert-butyl(dimethyl)silyl]oxy}phenyl)nicotinonitrile2×

Product 1

HCID 69145261N-{3-[2-amino-6-(2-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-3-cyano-4-pyridinyl]phenyl}-5-oxotetrahydro-2-furancarboxamideYield 77%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a cold (0° C.) mixture of pyridine (0.20 mL, 2.424 mmol), 2-amino-4-(3-aminophenyl)-6-(2-{[tert-butyl(dimethyl)silyl]oxy}phenyl)nicotinonitrile (starting compound 2, 1.010 g, 2.424 mmol), acetonitrile (10 mL) and THF (2 mL) was added dropwise a solution of 5-oxotetrahydro-2-furancarbonyl chloride (0.360 g, 2.424 mmol) in acetonitrile (4 mL). The mixture was stirred for 2 hrs., allowed to warm to room temperature, stirred for 1 hr., and extracted with ethyl acetate and water. The separated organic phase was washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica-gel (hexane:Ethyl acetate, 7:3-5:5) to give N-{3-[2-amino-6-(2-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-3-cyano-4-pyridinyl]phenyl}-5-oxotetrahydro-2-furancarboxamide as a white solid (0.982 g, yield 77%).

Workup

  1. stirringstirred for 1 hr
  2. extraction, and extracted with ethyl acetate and water
  3. washThe separated organic phase was washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography on silica-gel (hexane:Ethyl acetate, 7:3-5:5)

Sources & evidence

ORD record
ord-290e8f2f082f4ac5a18f433436e59295
Source dataset
uspto-grants-2008_08
Patent number
US07410986B2

Reaction notes

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