HCID 23599479, compound → HCID 23599477, compound

HRID 1350906Notes

Reaction equation

HRID 1350906 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][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([C:23]#[N:24])[CH:18]=3)=[CH:15][CH:16]=1)=[O:11])[CH2:2]2>CO.C(O)(=O)C.[Pd]>[N:1]12[CH2:6][CH2:5][CH:4]([CH2:7][CH2:8]1)[C@@H:3]([NH:9][C:10]([C:12]1[S:13][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([CH2:23][NH2:24])[CH:18]=3)=[CH:15][CH:16]=1)=[O:11])[CH2:2]2

Participants

5

Reactant 1

HCID 23599479HCID 23599479, compound

Product 1

HCID 23599477HCID 23599477, compoundYield 7.3%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

To the solution of (R)-N-(1-azabicyclo[2.2.2]oct-3-yl)(5-(3-cyanophenyl)thiophene-2-carboxamide) (311 mg) in methanol and acetic acid (1: 1,10 mL) a catalytic amount of 10% Pd-C was added and the mixture was hydrogenated at 50 p.s.i. for 36 hr. The mixture was filtered through a pad of celite. The residue was purified first by flash chromatography using 5–20% 3.5M methanolic ammonia/chloroform mixtures as the eluent and then by reverse phase IHPLC on a Waters Bondapak® C18 column using a gradient of acetonitrile and 0.1% aqueous trifluoroacetic acid as the eluent. The free base was prepared by basification of the product-containing fractions and extraction into chloroform followed by evaporation to gave the title compound (23 mg); MS (ES+) 342 (MH+).

Workup

  1. filtrationThe mixture was filtered through a pad of celite
  2. customThe residue was purified first by flash chromatography
  3. customThe free base was prepared by basification of the product-containing fractions and extraction into chloroform
  4. customfollowed by evaporation

Sources & evidence

ORD record
ord-cbdf8df46e5a4a2f826aef21ed2b2850
Source dataset
uspto-grants-2007_05
Patent number
US07214688B2

Reaction notes

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