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8-[(3S)-3-(acetylamino)pyrrolidin-1-yl]-5-chloro-N-methoxy-N-methylquinoline-7-carboxamide → N-[(3S)-1-(7-acetyl-5-chloroquinolin-8-yl)pyrrolidin-3-yl]acetamide

HRID 1192501
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1192501
[C:1]([NH:4][C@H:5]1[CH2:9][CH2:8][N:7]([C:10]2[C:11]([C:21](N(OC)C)=[O:22])=[CH:12][C:13]([Cl:20])=[C:14]3[C:19]=2[N:18]=[CH:17][CH:16]=[CH:15]3)[CH2:6]1)(=[O:3])[CH3:2].[CH3:27][Mg]Br>O1CCCC1>[C:21]([C:11]1[C:10]([N:7]2[CH2:8][CH2:9][C@H:5]([NH:4][C:1](=[O:3])[CH3:2])[CH2:6]2)=[C:19]2[C:14]([CH:15]=[CH:16][CH:17]=[N:18]2)=[C:13]([Cl:20])[CH:12]=1)(=[O:22])[CH3:27]
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Komponenten

4

Edukt 2

HCID 866561778-[(3S)-3-(acetylamino)pyrrolidin-1-yl]-5-chloro-N-methoxy-N-methylquinoline-7-carboxamideHCID 178418573HCID 178418573, Verbindung

Produkt 1

HCID 67249481N-[(3S)-1-(7-acetyl-5-chloroquinolin-8-yl)pyrrolidin-3-yl]acetamideAusbeute 33 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a mixture of 8-[(3S)-3-(acetylamino)pyrrolidin-1-yl]-5-chloro-N-methoxy-N-methylquinoline-7-carboxamide (75 mg, 0.20 mmol) in tetrahydrofuran (0.3 mL) was added 1.40 M methylmagnesium bromide in tetrahydrofuran (0.85 mL, 1.2 mmol). The reaction was stirred at room temperature overnight, quenched with saturated ammonium chloride, and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulfate, and then concentrated to dryness under reduced pressure. The resultant residue was purified on silica gel, eluting with 0 to 10% MeOH in dichloromethane, to give the desired product (22 mg, 33%). LCMS calculated for C17H19ClN3O2(M+H)+: m/z=332.1; found: 332.1.

Aufarbeitung

  1. customquenched with saturated ammonium chloride
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated to dryness under reduced pressure
  6. customThe resultant residue was purified on silica gel
  7. washeluting with 0 to 10% MeOH in dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-25cbb71db5f347e693548f2c29fa242b
Quelldatensatz
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08680108B2

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