Stannane, tributyl(methoxymethyl)- → HCID 57608271, compound

HRID 1171207Notes

Reaction equation

HRID 1171207 reaction equation
[NH2:1][C:2]1[C:7]([C:8]([NH:10][CH2:11][C:12]2[O:13][C:14]3[CH:20]=[C:19](OS(C(F)(F)F)(=O)=O)[CH:18]=[CH:17][C:15]=3[CH:16]=2)=[O:9])=[CH:6][CH:5]=[C:4]([CH2:29][O:30][CH3:31])[N:3]=1.C([Sn](CCCC)(CCCC)[CH2:37][O:38][CH3:39])CCC>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].CN1CCCC1=O>[NH2:1][C:2]1[N:3]=[C:4]([CH2:29][O:30][CH3:31])[CH:5]=[CH:6][C:7]=1[C:8]([NH:10][CH2:11][C:12]1[O:13][C:14]2[CH:20]=[C:19]([CH2:37][O:38][CH3:39])[CH:18]=[CH:17][C:15]=2[CH:16]=1)=[O:9]

Participants

6

Reactant 2

HCID 11088958Stannane, tributyl(methoxymethyl)-HCID 57608187HCID 57608187, compound

Product 1

HCID 57608271HCID 57608271, compoundYield 6%

Reagents, catalysts & solvents 3

HCID 70681Tetrabutylammonium ChlorideCatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
135 °C

Procedure

To a 1-methyl-2-pyrrolidinone (500 μL) solution of trifluoromethanesulfonic acid 2-(((2-amino-6-methoxymethyl-pyridin-3-carbonyl)-amino)-methyl)-benzofuran-6-yl ester (15 mg, 33 μmol) described in Production Example 47-1 were added tributyl-methoxymethyl-stannane (14 mg, 43 μmol), tetrakis(triphenylphosphine)palladium (0) (3.78 mg, 3.3 μmol) and tetrabutyl ammonium chloride (1.82 mg, 6.5 μmol) at room temperature, which was stirred at 135° C. for 4 hours under nitrogen atmosphere. After allowing the reaction solution to cool to room temperature, the reaction solution was filtered and purified by reverse phase high-performance liquid chromatography (using an acetonitrile-aqueous mobile phase (containing 0.1% trifluoroacetic acid)) followed by further purifying by silica gel column chromatography (ethyl acetate) to obtain the title compound (0.7 mg, 6%) as a white solid.

Workup

  1. temperatureto cool to room temperature
  2. filtrationthe reaction solution was filtered
  3. custompurified by reverse phase high-performance liquid chromatography (
  4. additionan acetonitrile-aqueous mobile phase (containing 0.1% trifluoroacetic acid))
  5. customby further purifying by silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-7e1f6b692aab4528bf356beb12aee2b3
Source dataset
uspto-grants-2010_11
Patent number
US07829585B2

Reaction notes

Loading…