Hydrochloric Acid → (2Z)-3-(5-chloro-6-{[(3R)-1-cyclopentyl-3-pyrrolidinyl]amino}-3-pyridinyl)-2-fluoroacrylic acid

HRID 226440Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 226440
[Cl:1][C:2]1[CH:3]=[C:4](/[CH:19]=[C:20](\[F:26])/[C:21]([O:23]CC)=[O:22])[CH:5]=[N:6][C:7]=1[NH:8][C@@H:9]1[CH2:13][CH2:12][N:11]([CH:14]2[CH2:18][CH2:17][CH2:16][CH2:15]2)[CH2:10]1.[OH-].[Na+].Cl>CO>[Cl:1][C:2]1[CH:3]=[C:4](/[CH:19]=[C:20](\[F:26])/[C:21]([OH:23])=[O:22])[CH:5]=[N:6][C:7]=1[NH:8][C@@H:9]1[CH2:13][CH2:12][N:11]([CH:14]2[CH2:15][CH2:16][CH2:17][CH2:18]2)[CH2:10]1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86603745ethyl (2Z)-3-(5-chloro-6-([(3R)-1-cyclopentyl-3-pyrrolidinyl]amino)-3-pyridinyl)-2-fluoroacrylate

Produkt 1

HCID 68960084(2Z)-3-(5-chloro-6-{[(3R)-1-cyclopentyl-3-pyrrolidinyl]amino}-3-pyridinyl)-2-fluoroacrylic acidAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
77.5 °C

Versuchsvorschrift

A mixture of ethyl (2Z)-3-(5-chloro-6-{[(3R)-1-cyclopentyl-3-pyrrolidinyl]amino}-3-pyridinyl)-2-fluoroacrylate (710 mg) and 1N NaOH solution (3.8 ml) in MeOH (20 ml) was stirred at 75-80° C. for 2 hours. To the reaction mixture was added 1N HCl solution (3.8 ml) and the resultant solution was evaporated in vacuo and the residue was dissolved in a mixture of MeOH and toluene and evaporated in vacuo and the residue was dried to give (2Z)-3-(5-chloro-6-{[(3R)-1-cyclopentyl-3-pyrrolidinyl]amino}-3-pyridinyl)-2-fluoroacrylic acid (658 mg).

Aufarbeitung

  1. customthe resultant solution was evaporated in vacuo
  2. dissolutionthe residue was dissolved in a mixture of MeOH and toluene
  3. customevaporated in vacuo
  4. customthe residue was dried

Quellen und Nachweise

ORD-Eintrag
ord-2ec5cec2e91f40a1a101d78345adfdb1
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07557127B2

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