Sodium Carbonate → HCID 23599448, compound

HRID 1726344Notes

Reaction equation

HRID 1726344 reaction equation
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C@@H:3]([NH:9][C:10]([C:12]1[O:13][C:14](Br)=[CH:15][CH:16]=1)=[O:11])[CH2:2]2.[C:18]([NH:21][C:22]1[CH:23]=[C:24](B(O)O)[CH:25]=[CH:26][CH:27]=1)(=[O:20])[CH3:19].C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C@@H:3]([NH:9][C:10]([C:12]1[O:13][C:14]([C:26]3[CH:25]=[CH:24][CH:23]=[C:22]([NH:21][C:18](=[O:20])[CH3:19])[CH:27]=3)=[CH:15][CH:16]=1)=[O:11])[CH2:2]2

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 157274(3-Acetamidophenyl)boronic acidHCID 952706HCID 952706, compound

Product 1

HCID 23599448HCID 23599448, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

Prepared by a method analogous to that described in Example 1 from (R)-N-(1-azabicyclo[2.2.2]oct-3-yl)(5-bromofuran-2-carboxamide) and 3-(N-acetylamino)phenylboronic acid, using tetrakis(triphenylphosphine)palladium(0) and sodium carbonate in a mixture of 1,2-dimethoxyethane and water. The compound was purified by reverse phase HPLC on a Waters Bondapak® C18 column using a gradient of acetonitrile and 0.1% aqueous trifluoroacetic acid as the eluent. The product-containing fractions were then evaporated and the residue dissolved in methanol. Excess hydrogen chloride solution (1M in diethyl ether) was added and the solution was evaporated. Recrystallisation from methanol/diethyl ether gave the hydrochloride salt of the title compound as a yellow solid; MS (ES+) 354 (MH+).

Workup

  1. customPrepared by a method analogous to
  2. customThe compound was purified by reverse phase HPLC on a Waters Bondapak® C18 column
  3. customThe product-containing fractions were then evaporated
  4. dissolutionthe residue dissolved in methanol
  5. additionExcess hydrogen chloride solution (1M in diethyl ether) was added
  6. customthe solution was evaporated
  7. customRecrystallisation from methanol/diethyl ether

Sources & evidence

ORD record
ord-2852b19bdcda4ed3b648d970c596c949
Source dataset
uspto-grants-2009_02
Patent number
US07491734B2

Reaction notes

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