Pyridine → HCID 12512124, compound

HRID 250189Notes

Reaction equation

HRID 250189 reaction equation
N1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH:10]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:11]2[C:16](=[O:17])OC(C)(C)OC2=O)=C1.[CH3:27][NH2:28].[N:29]1C=CC=C[CH:30]=1>>[NH:28]1[C:5]2[C:4](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:3]([CH:10]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH2:11][C:16]([NH:29][CH3:30])=[O:17])=[CH:27]1

Participants

4

Reactant 3

HCID 1049PyridineHCID 6329MethylamineHCID 111318571,3-Dioxane-4,6-dione, 5-(1H-indol-3-ylphenylmethyl)-2,2-dimethyl-

Product 1

HCID 12512124HCID 12512124, compoundYield 85%

Procedure

5-[(1H-Indol-3-yl)-phenyl-methyl]-2,2-dimethyl-[1,3]dioxane-4,6-dione (0.500 g) was dissolved in dry pyridine (5 ml) in a sealable test tube. To this solution was added methyl amine (2.0 ml, 2M in THF) and the tube was sealed and immersed in an oil bath which had been preheated to 120° C. The tube was heated at this temperature for 2 hours, after which time it was cooled and diluted with ice water. The product was extracted into ethyl acetate, washed with dilute HCl, dried (MgSO4) and evaporated to dryness to afford 0.338 g of 3-(1H-indol-3-yl)-N-methyl-3-phenyl-propionamide, (85%, MS (M+H)=279), which was used in the following step without further purification.

Workup

  1. customthe tube was sealed
  2. customimmersed in an oil bath
  3. customhad been preheated to 120° C
  4. temperatureThe tube was heated at this temperature for 2 hours
  5. temperatureafter which time it was cooled
  6. extractionThe product was extracted into ethyl acetate
  7. washwashed with dilute HCl
  8. dry with materialdried (MgSO4)
  9. customevaporated to dryness

Sources & evidence

ORD record
ord-7f0d86f0ea5541c69116b72b85d567f0
Source dataset
uspto-grants-2011_01
Patent number
US07863305B2

Reaction notes

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