1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → (R)-(6-Aminopyridin-3-yl)(3-methylmorpholino)methanone

HRID 407716Notes

Reaction equation

HRID 407716 reaction equation
[CH3:1][C@@H:2]1[CH2:7][O:6][CH2:5][CH2:4][NH:3]1.C(N=C=NCCCN(C)C)C.OC1C2N=NNC=2C=CC=1.[NH2:29][C:30]1[CH:38]=[CH:37][C:33]([C:34](O)=[O:35])=[CH:32][N:31]=1>C(O)C>[NH2:29][C:30]1[N:31]=[CH:32][C:33]([C:34]([N:3]2[CH2:4][CH2:5][O:6][CH2:7][C@H:2]2[CH3:1])=[O:35])=[CH:37][CH:38]=1

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 184966-Aminonicotinic acidHCID 641498(R)-3-MethylmorpholineHCID 178418300HCID 178418300, compound

Product 1

HCID 86683985(R)-(6-Aminopyridin-3-yl)(3-methylmorpholino)methanoneYield 49.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (R)-3-methylmorpholine (2.02 g, 20 mmol) in ethanol (25 mL) was added 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide (EDCI) (3.33 g, 17.4 mmol), hydroxybenzotriazole (HOBt) (2.35 g, 17.4 mmol), and 6-aminonicotinic acid (2.0 g, 14.5 mmol). After stirring for 18 h at room temperature, the reaction suspension was filtered and the filtrate was concentrated under reduced pressure. The residue was purified by silica-gel column chromatography eluting with 3:1 ethyl acetate/petroleum ether to afford 132a as a white solid (1.6 g, 36%). MS-ESI: [M+H]+ 222.3.

Workup

  1. filtrationthe reaction suspension was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by silica-gel column chromatography
  4. washeluting with 3:1 ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-0b5cd509ea6c40b595edb24485f3f720
Source dataset
uspto-grants-2014_06
Patent number
US08754077B2

Reaction notes

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