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Trifluoroacetic acid → 4-{[cis-3-(aminomethyl)-4-hydroxy-1-piperidinyl]methyl}-3-fluoro-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one

HRID 15341
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 15341
[F:1][C:2]1[CH:3]=[N:4][C:5]2[CH:6]=[CH:7][C:8](=[O:27])[N:9]3[CH2:13][CH:12]([CH2:14][N:15]4[CH2:20][CH2:19][C@H:18]([OH:21])[C@H:17]([CH2:22][NH:23]C(=O)[O-])[CH2:16]4)[C:11]=1[C:10]=23.FC(F)(F)C(O)=O>ClCCl>[NH2:23][CH2:22][C@H:17]1[C@@H:18]([OH:21])[CH2:19][CH2:20][N:15]([CH2:14][CH:12]2[C:11]3=[C:2]([F:1])[CH:3]=[N:4][C:5]4[CH:6]=[CH:7][C:8](=[O:27])[N:9]([C:10]=43)[CH2:13]2)[CH2:16]1
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Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 86630582{(cis-1-[(3-fluoro-7-oxo-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-4-yl)methyl]-4-hydroxy-3-piperidinyl}methyl)carbamate

Produkt 1

HCID 686844234-{[cis-3-(aminomethyl)-4-hydroxy-1-piperidinyl]methyl}-3-fluoro-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-oneAusbeute 59,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344Dichloromethane
Lösungsmittel

Versuchsvorschrift

A suspension of 1,1-dimethylethyl({(cis-1-[(3-fluoro-7-oxo-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-4-yl)methyl]-4-hydroxy-3-piperidinyl}methyl)carbamate (0.175 g, 0.405 mmol) in dichloromethane (2 ml) was treated with trifluoroacetic acid (1 ml) and stirred at room temperature for 20 min. The reaction mixture was evaporated and then redissolved using a 4:1 dichloromethane:methanol solution. The organic phase was then treated with aqueous sodium bicarbonate solution. The aqueous phase was extracted 10 times with a 4:1 dichloromethane:methanol solution and then the combined organic phases were dried and the solvent was removed under reduced pressure and the residue was subjected to column chromatography on silica gel using a dichloromethane, methanol and ammonia gradient to provide the desired compound (0.08 g).

Aufarbeitung

  1. customThe reaction mixture was evaporated
  2. dissolutionredissolved
  3. additionThe organic phase was then treated with aqueous sodium bicarbonate solution
  4. extractionThe aqueous phase was extracted 10 times with a 4:1 dichloromethane
  5. dry with materialmethanol solution and then the combined organic phases were dried
  6. customthe solvent was removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-dffa17a8d0c4468ba2674302e125925d
Quelldatensatz
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07732461B2

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