4-Ethenyl-6-(methyloxy)-1,5-naphthyridine-3-carbonitrile → N-[((3S,4S)-1-{2-[3-cyano-6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-4-hydroxy-3-pyrrolidinyl)methyl]-2,2,2-trifluoroacetamide

HRID 639133Notes

Reaction equation

HRID 639133 reaction equation
Cl.[F:2][C:3]([F:15])([F:14])[C:4]([NH:6][CH2:7][C@@H:8]1[C@H:12]([OH:13])[CH2:11][NH:10][CH2:9]1)=[O:5].[CH:16]([C:18]1[C:27]2[C:22](=[CH:23][CH:24]=[C:25]([O:28][CH3:29])[N:26]=2)[N:21]=[CH:20][C:19]=1[C:30]#[N:31])=[CH2:17]>C(O)C>[C:30]([C:19]1[CH:20]=[N:21][C:22]2[C:27]([C:18]=1[CH2:16][CH2:17][N:10]1[CH2:11][C@@H:12]([OH:13])[C@@H:8]([CH2:7][NH:6][C:4](=[O:5])[C:3]([F:2])([F:14])[F:15])[CH2:9]1)=[N:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=2)#[N:31]

Participants

4

Reactant 2

HCID 592543544-Ethenyl-6-(methyloxy)-1,5-naphthyridine-3-carbonitrileHCID 866168202,2,2-trifluoro-N-{[(3R,4S)-4-hydroxy-3-pyrrolidinyl]methyl}acetamide HCl

Product 1

HCID 59026184N-[((3S,4S)-1-{2-[3-cyano-6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-4-hydroxy-3-pyrrolidinyl)methyl]-2,2,2-trifluoroacetamideYield 47.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
95 °C

Procedure

To 2,2,2-trifluoro-N-{[(3R,4S)-4-hydroxy-3-pyrrolidinyl]methyl}acetamide HCl (0.137 g, 0.552 mmol) was added EtOH (2.0 mL). 4-ethenyl-6-(methyloxy)-1,5-naphthyridine-3-carbonitrile (0.117 g, 0.552 mmol) was added to the mixture along with TEA (0.231 mL, 1.66 mmol) and the reaction was heated and stirred at 95 degrees C. for 18 hours, allowing the ethanol to evaporate. The solution was concentrated under reduced pressure and was chromatographed on silica gel to yield an oil (0.110 g, 47%). LCMS: m/z 424.4 (MH+).

Workup

  1. temperaturethe reaction was heated
  2. customto evaporate
  3. concentrationThe solution was concentrated under reduced pressure
  4. customwas chromatographed on silica gel

Sources & evidence

ORD record
ord-cb90c444684747d1914533acc086204f
Source dataset
uspto-grants-2010_04
Patent number
US07691850B2

Reaction notes

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