HCID 57928188, compound → HCID 57928180, compound

HRID 1360192Notes

Reaction equation

HRID 1360192 reaction equation
[C:1]([C:4]12[CH2:13][CH:8]3[CH2:9][CH:10]([CH2:12][CH:6]([CH:7]3[NH:14][C:15]3[C:20]([C:21]([O:23]CC4C=CC=CC=4)=[O:22])=[CH:19][N:18]=[C:17]4[NH:31][CH:32]=[CH:33][C:16]=34)[CH2:5]1)[CH2:11]2)(=[O:3])[NH2:2].[H][H]>[Pd].CO.O1CCOCC1>[C:1]([C:4]12[CH2:13][CH:8]3[CH2:9][CH:10]([CH2:12][CH:6]([CH:7]3[NH:14][C:15]3[C:20]([C:21]([OH:23])=[O:22])=[CH:19][N:18]=[C:17]4[NH:31][CH:32]=[CH:33][C:16]=34)[CH2:5]1)[CH2:11]2)(=[O:3])[NH2:2]

Participants

6

Reactant 2

HCID 57928188HCID 57928188, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 57928180HCID 57928180, compoundYield 80.2%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

10% Palladium on carbon (50% wet) (40 mg) was added to a solution of benzyl 4-[(5-carbamoyladamantan-2-yl)amino]-1H-pyrrolo-[2,3-b]pyridine-5-carboxylate (183 mg) in methanol (5 ml) and 1,4-dioxane (5 ml), and hydrogenated under hydrogen atmosphere for 5 hours. Resulting precipitates were dissolved by tetrahydrofuran and filtered out the catalysts. The filtrates were evaporated in vacuo to give 4-[(5-carbamoyladamantan-2-yl)amino]-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid (117 mg).

Workup

  1. customResulting
  2. customprecipitates
  3. dissolutionwere dissolved by tetrahydrofuran
  4. filtrationfiltered out the catalysts
  5. customThe filtrates were evaporated in vacuo

Sources & evidence

ORD record
ord-641397728ae942bd8571118aedd19e76
Source dataset
uspto-grants-2011_02
Patent number
US07879844B2

Reaction notes

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