Triethylamine → HCID 21249892, compound

HRID 1532389Notes

Reaction equation

HRID 1532389 reaction equation
C12N(C(=O)C(C3C=C4C(=CC=3)NC(C3C=C(C)C=C(C)C=3)=C4CCN[C:32]([CH3:44])([CH3:43])[CH:33]=[CH:34][CH:35]([OH:42])[C:36]3[CH:41]=[CH:40][N:39]=[CH:38][CH:37]=3)(C)C)C(CC1)CC2.FC(F)(F)C(OC(=O)C(F)(F)F)=O.C(N(CC)CC)C.[H][H]>O1CCCC1.C(OCC)(=O)C.[OH-].[OH-].[Pd+2].C(O)(=O)C>[CH3:43][C:32]([CH3:44])=[CH:33][CH:34]1[O:42][CH:35]1[C:36]1[CH:41]=[CH:40][N:39]=[CH:38][CH:37]=1

Participants

9

Reactant 4

HCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 54262527HCID 54262527, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 21249892HCID 21249892, compound

Reagents, catalysts & solvents 4

HCID 9942167Palladium hydroxideCatalystHCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-(7-azabicyclo[2.2.1]hept-7-yl)-2-{2-(3,5-dimethylphenyl)-3-[2-(4-hydroxy-1,1-dimethyl-4-pyridin-4-yl-but-2-enylamino)ethyl]-1H-indol-5-yl}-2-methylpropan-1-one (27 mg in a mixture of 2 mL dry tetrahydrofuran and 2 mL ethyl acetate) at 0° C. was added 0.010 mL trifluoroacetic anhydride followed by 0.009 mL triethylamine and the mixture stirred at low temperature. After 15 minutes, 0.030 mL acetic acid was added and along with 28 mg palladium hydroxide on carbon. The reaction flask was fitted with a hydrogen balloon, evacuated and recharged with hydrogen (3 times) and stirred at room temperature. After 8 hours the reaction was flushed with nitrogen, filtered over diatomaceous earth and concentrated in vacuo. Purification by flash chromatography on silica gel (methylene chloride:methanol:ammonium hydroxide, 94:6:1) gave the title compound (15 mg). m/e=591 (M+H).

Workup

  1. customevacuated
  2. stirringstirred at room temperature
  3. customAfter 8 hours the reaction was flushed with nitrogen
  4. filtrationfiltered over diatomaceous earth
  5. concentrationconcentrated in vacuo
  6. customPurification by flash chromatography on silica gel (methylene chloride:methanol:ammonium hydroxide, 94:6:1)

Sources & evidence

ORD record
ord-bb63a543b8b44061bd6b8f247bd3fcba
Source dataset
uspto-grants-2001_03
Patent number
US06200957B1

Reaction notes

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