Hydrochloric Acid → HCID 10154805, compound

HRID 1726348Notes

Reaction equation

HRID 1726348 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[S:13][CH:14]=[C:15](Br)[CH:16]=1)=[O:11])[CH2:2]2.[C:18]1(B(O)O)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(=O)([O-])[O-].[Na+].[Na+].Cl>O1CCCC1.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.O.C(O)C>[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C@@H:3]([NH:9][C:10]([C:12]1[S:13][CH:14]=[C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH:16]=1)=[O:11])[CH2:2]2

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 23599474HCID 23599474, compound

Product 1

HCID 10154805HCID 10154805, compound

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Prepared by a method analogous to that described in Example 1 from (R)-N-(1-Aza-bicyclo[2.2.2]oct-3-yl)(4-bromothiophene-2-carboxamide) and phenylboronic acid, using tetrakis(triphenylphosphine)palladium(0) and sodium carbonate in a mixture of tetrahydrofuran, ethanol, 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 hydrochloride salt was prepared by evaporation of the product-containing fractions, dissolution of the residue in methanol, addition of excess hydrogen chloride solution (1M in diethyl ether) and evaporation. Recrystallisation from ethyl acetate gave the hydrochloride salt of the title compound as a colourless solid; MS (ES+) 313 (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 hydrochloride salt was prepared by evaporation of the product-containing fractions, dissolution of the residue in methanol
  4. customRecrystallisation from ethyl acetate

Sources & evidence

ORD record
ord-66c1b2d44c144bdf892e0ffafd7f6e52
Source dataset
uspto-grants-2009_02
Patent number
US07491734B2

Reaction notes

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