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

HRID 639134Notes

Reaction equation

HRID 639134 reaction equation
[C:1]([C:3]1[CH:4]=[N:5][C:6]2[C:11]([C:12]=1[CH2:13][CH2:14][N:15]1[CH2:19][C@@H:18]([OH:20])[C@@H:17]([CH2:21][NH:22]C(=O)C(F)(F)F)[CH2:16]1)=[N:10][C:9]([O:29][CH3:30])=[CH:8][CH:7]=2)#[N:2]>CO>[NH2:22][CH2:21][C@@H:17]1[C@H:18]([OH:20])[CH2:19][N:15]([CH2:14][CH2:13][C:12]2[C:11]3[C:6](=[CH:7][CH:8]=[C:9]([O:29][CH3:30])[N:10]=3)[N:5]=[CH:4][C:3]=2[C:1]#[N:2])[CH2:16]1

Participants

3

Reactant 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-trifluoroacetamide

Product 1

HCID 590260824-{2-[(3S,4S)-3-(aminomethyl)-4-hydroxy-1-pyrrolidinyl]ethyl}-6-(methyloxy)-1,5-naphthyridine-3-carbonitrile

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N-[((3S,4S)-1-{2-[3-cyano-6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-4-hydroxy-3-pyrrolidinyl)methyl]-2,2,2-trifluoroacetamide (0.110 g, 0.26 mmol) was dissolved in methanol (5 mL). 10% aqueous K CO was added to the original solution and it was stirred at ambient temperature for 2 hours. The solution was extracted 3× with chloroform and washed with brine. The solvent was removed under reduced pressure. (0.076 g, 89%) LCMS: m/z 328.6 (MH+).

Workup

  1. addition10% aqueous K CO was added to the original solution and it
  2. extractionThe solution was extracted 3× with chloroform
  3. washwashed with brine
  4. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-eeccaba552c5486f8913f256e2f0b00d
Source dataset
uspto-grants-2010_04
Patent number
US07691850B2

Reaction notes

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