[(2R)-3-{2-[6-(1-Azetidinyl)-5-fluoro-2-methyl-4-pyrimidinyl]hydrazino}-2-(cyclopentylmethyl)-3-oxopropyl][(phenylmethyl)oxy]formamide → [(2R)-3-{2-[6-(1-azetidinyl)-5-fluoro-2-methyl-4-pyrimidinyl]hydrazino}-2-(cyclopentylmethyl)-3-oxopropyl]hydroxyformamide

HRID 1366407Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1366407
[N:1]1([C:5]2[N:10]=[C:9]([CH3:11])[N:8]=[C:7]([NH:12][NH:13][C:14](=[O:34])[C@H:15]([CH2:28][CH:29]3[CH2:33][CH2:32][CH2:31][CH2:30]3)[CH2:16][N:17]([O:20]CC3C=CC=CC=3)[CH:18]=[O:19])[C:6]=2[F:35])[CH2:4][CH2:3][CH2:2]1>CO>[N:1]1([C:5]2[N:10]=[C:9]([CH3:11])[N:8]=[C:7]([NH:12][NH:13][C:14](=[O:34])[C@H:15]([CH2:28][CH:29]3[CH2:30][CH2:31][CH2:32][CH2:33]3)[CH2:16][N:17]([OH:20])[CH:18]=[O:19])[C:6]=2[F:35])[CH2:2][CH2:3][CH2:4]1

Komponenten

3

Edukt 1

HCID 86636927[(2R)-3-{2-[6-(1-Azetidinyl)-5-fluoro-2-methyl-4-pyrimidinyl]hydrazino}-2-(cyclopentylmethyl)-3-oxopropyl][(phenylmethyl)oxy]formamide

Produkt 1

HCID 58000754[(2R)-3-{2-[6-(1-azetidinyl)-5-fluoro-2-methyl-4-pyrimidinyl]hydrazino}-2-(cyclopentylmethyl)-3-oxopropyl]hydroxyformamideAusbeute 98,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

[(2R)-3-{2-[6-(1-Azetidinyl)-5-fluoro-2-methyl-4-pyrimidinyl]hydrazino}-2-(cyclopentylmethyl)-3-oxopropyl][(phenylmethyl)oxy]formamide (3.9 g, 8.0 mmol) was dissolved in 50 mL of MeOH and degassed with argon. 10% Pd/C (400 mg) was added, and the contents were placed under a hydrogen balloon for 4.5 h. The contents were then degassed with argon and filtered through Celite, and the Celite pad was washed with DCM and MeOH. The resulting filtrate was concentrated in vacuo to provide the pure [(2R)-3-{2-[6-(1-azetidinyl)-5-fluoro-2-methyl-4-pyrimidinyl]hydrazino}-2-(cyclopentylmethyl)-3-oxopropyl]hydroxyformamide (3.1 g, 98%). LCMS: (M+H)+: 395.

Aufarbeitung

  1. customdegassed with argon
  2. addition10% Pd/C (400 mg) was added
  3. customfor 4.5 h
  4. customThe contents were then degassed with argon
  5. filtrationfiltered through Celite
  6. washthe Celite pad was washed with DCM and MeOH
  7. concentrationThe resulting filtrate was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-591198adafc34d91af461e364b2c63fc
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07893056B2

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