Hydrazine → (S)-5-amino-2-(3-(2-chloro-3-fluorobenzyl)-1-methylureido)pentyl 5-(trifluoromethyl)pyridin-2-ylcarbamate

HRID 409785

Reaktionsgleichung

Reaktionsgleichung von HRID 409785
[F:1][C:2]([F:44])([F:43])[C:3]1[CH:4]=[CH:5][C:6]([NH:9][C:10](=[O:42])[O:11][CH2:12][C@@H:13]([N:28]([CH3:41])[C:29]([NH:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[C:35]([F:39])[C:34]=2[Cl:40])=[O:30])[CH2:14][CH2:15][CH2:16][N:17]2C(=O)C3C(=CC=CC=3)C2=O)=[N:7][CH:8]=1.NN>CO>[F:44][C:2]([F:1])([F:43])[C:3]1[CH:4]=[CH:5][C:6]([NH:9][C:10](=[O:42])[O:11][CH2:12][C@@H:13]([N:28]([CH3:41])[C:29]([NH:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[C:35]([F:39])[C:34]=2[Cl:40])=[O:30])[CH2:14][CH2:15][CH2:16][NH2:17])=[N:7][CH:8]=1

Komponenten

4

Edukt 2

HCID 9321HydrazineHCID 57947787(S)-2-(3-(2-chloro-3-fluorobenzyl)-1-methylureido)-5-(1,3-dioxoisoindolin-2-yl)pentyl 5-(trifluoromethyl)pyridin-2-ylcarbamate

Produkt 1

HCID 57947682(S)-5-amino-2-(3-(2-chloro-3-fluorobenzyl)-1-methylureido)pentyl 5-(trifluoromethyl)pyridin-2-ylcarbamateAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of (S)-2-(3-(2-chloro-3-fluorobenzyl)-1-methylureido)-5-(1,3-dioxoisoindolin-2-yl)pentyl 5-(trifluoromethyl)pyridin-2-ylcarbamate (150 mg, 0.24 mmol) in MeOH (5.0 mL) was added NH2NH2 (0.2 mL). The reaction mixture was stirred at RT for 2 h. The mixture was concentrated, dissolved in MeOH, filtered, and purified on RP-HPLC using a mixture of acetonitrile and H2O to give (S)-5-amino-2-(3-(2-chloro-3-fluorobenzyl)-1-methylureido)pentyl 5-(trifluoromethyl)pyridin-2-ylcarbamate (91 mg, 76%). LRMS (M+H+) m/z 506.1.

Aufarbeitung

  1. concentrationThe mixture was concentrated
  2. dissolutiondissolved in MeOH
  3. filtrationfiltered
  4. custompurified on RP-HPLC
  5. additiona mixture of acetonitrile and H2O

Quellen und Nachweise

ORD-Eintrag
ord-e43f5077979d4b5ca89df5e32617c922
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08759374B2

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