3-Aminopyridine → HCID 57626005, compound

HRID 546632Notes

Reaction equation

HRID 546632 reaction equation
[CH3:1][O:2][C:3](=[O:30])[C:4]([C:7]1[CH:12]=[CH:11][C:10]([N:13]2[C:17](=[O:18])[C:16]([CH3:20])([CH3:19])[N:15]([CH2:21][C:22]3[CH:27]=[CH:26][N:25]=[C:24](Cl)[CH:23]=3)[C:14]2=[O:29])=[CH:9][CH:8]=1)([CH3:6])[CH3:5].[NH2:31][C:32]1[CH:33]=[N:34][CH:35]=[CH:36][CH:37]=1.CC1(C)C2C=CC(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=2OC2C1=CC=C(P(C1C=CC=CC=1)C1C=CC=CC=1)C=2.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:19][C:16]1([CH3:20])[C:17](=[O:18])[N:13]([C:10]2[CH:11]=[CH:12][C:7]([C:4]([CH3:6])([CH3:5])[C:3]([O:2][CH3:1])=[O:30])=[CH:8][CH:9]=2)[C:14](=[O:29])[N:15]1[CH2:21][C:22]1[CH:27]=[CH:26][N:25]=[C:24]([NH:31][C:32]2[CH:33]=[N:34][CH:35]=[CH:36][CH:37]=2)[CH:23]=1

Participants

7

Reactant 4

HCID 100093-AminopyridineHCID 10796Cesium carbonateHCID 57625981HCID 57625981, compoundHCID 86628973(9,9-dimethyl-9H-xanthene-3,6-diyl)bis(diphenylphosphine)

Product 1

HCID 57626005HCID 57626005, compoundYield 68.8%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 1.23 g of 2-{4-[3-(2-chloropyridin-4-ylmethyl)-4,4-dimethyl-2,5-dioxo-imidazolidin-1-yl]-phenyl}-2-methylpropionic acid methyl ester obtained in stage d) below in 40 mL of dioxane are successively added, under argon, 0.4 g of 3-aminopyridine, 0.16 g of (9,9-dimethyl-9H-xanthene-3,6-diyl)bis(diphenylphosphine) (Xantphos), 0.065 g of palladium acetate and 3.65 g of caesium carbonate. The reaction mixture is refluxed for 4 hours and then filtered and concentrated under reduced pressure. The residue is purified by chromatography on a column of silica, eluting with a mixture of dichloromethane and methanol (98/02 by volume) to give 0.96 g of methyl 2-[4-(4,4-dimethyl-2,5-dioxo-3-{[2-(pyridin-3-ylamino)pyridin-4-yl]methyl}imidazolidin-1-yl)phenyl]-2-methylpropanoate, the characteristics of which are as follows:

Workup

  1. temperatureThe reaction mixture is refluxed for 4 hours
  2. filtrationfiltered
  3. concentrationconcentrated under reduced pressure
  4. customThe residue is purified by chromatography on a column of silica
  5. washeluting with a mixture of dichloromethane and methanol (98/02 by volume)

Sources & evidence

ORD record
ord-b3b4a1c66fc14392af8086bc90318266
Source dataset
uspto-grants-2011_05
Patent number
US07935819B2

Reaction notes

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