Methylamine → HCID 68552631, compound

HRID 1869183Notes

Reaction equation

HRID 1869183 reaction equation
CC1(C)[O:7][C:6](=O)[CH:5]([CH:9]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:10]2[C:18]3[C:13](=[N:14][CH:15]=[CH:16][CH:17]=3)[NH:12][CH:11]=2)C(=O)O1.[CH3:27][NH2:28]>N1C=CC=CC=1>[CH3:27][NH:28][C:6](=[O:7])[CH2:5][CH:9]([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[C:10]1[C:18]2[C:13](=[N:14][CH:15]=[CH:16][CH:17]=2)[NH:12][CH:11]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 68556789HCID 68556789, compound

Product 1

HCID 68552631HCID 68552631, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
120 °C

Procedure

A sealed tube loaded with 2,2-dimethyl-5-[phenyl-(1H-pyrrolo[2,3-b]pyridin-3-yl)-methyl]-[1,3]dioxane-4,6-dione (700 mg), methylamine (2M in THF, 3 ml) and pyridine (5 ml) was stirred at 120° C. for 2 hours. The reaction mixture was cooled to RT and partitioned between H2O and EtOAc. The organic layer was separated, dried over Na2SO4, filtered, concentrated, and purified via flash chromatography (hexane/EtOAc) affording N-Methyl-3-phenyl-3-(1H-pyrrolo[2,3-b]pyridin-3-yl)-propionamide.

Workup

  1. temperatureThe reaction mixture was cooled to RT
  2. custompartitioned between H2O and EtOAc
  3. customThe organic layer was separated
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified via flash chromatography (hexane/EtOAc)

Sources & evidence

ORD record
ord-b0f9cf090fc64cfb88c9564663f80026
Source dataset
uspto-grants-2009_12
Patent number
US07638517B2

Reaction notes

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