Hydrochloric Acid → HCID 57762534, Verbindung

HRID 230365Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 230365
CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.[CH3:23][O:24][C:25](=[O:45])[CH:26]([NH2:44])[CH2:27][CH:28]=[CH:29][C:30]1[CH:35]=[CH:34][C:33]([N:36]([CH3:43])[C:37]2[N:42]=[CH:41][CH:40]=[CH:39][N:38]=2)=[CH:32][CH:31]=1.[Cl:46][C:47]1[CH:55]=[CH:54][CH:53]=[C:52]([F:56])[C:48]=1[C:49](O)=[O:50].Cl>ClCCl>[CH3:23][O:24][C:25](=[O:45])[CH:26]([NH:44][C:49](=[O:50])[C:48]1[C:52]([F:56])=[CH:53][CH:54]=[CH:55][C:47]=1[Cl:46])[CH2:27]/[CH:28]=[CH:29]/[C:30]1[CH:31]=[CH:32][C:33]([N:36]([CH3:43])[C:37]2[N:42]=[CH:41][CH:40]=[CH:39][N:38]=2)=[CH:34][CH:35]=1

Komponenten

7

Edukt 5

HCID 313Hydrochloric AcidHCID 679472-Chloro-6-fluorobenzoic acidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 669119952-Amino-5-[4-(methyl-pyrimidin-2-ylamino)phenyl]pent-4-enoic acid methyl ester

Produkt 1

HCID 57762534HCID 57762534, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Under an argon atmosphere, EDC hydrochloride (39 mg) and HOBT (3 mg) were added to a solution of 2-amino-5-[4-(methyl-pyrimidin-2-ylamino)phenyl]pent-4-enoic acid methyl ester (51 mg) and 2-chloro-6-fluorobenzoic acid in dichloromethane (1.5 ml), and the resulting mixture was stirred at room temperature for 28 hours. To the reaction solution, 1N hydrochloric acid was added, and the resulting mixture was extracted with ethyl acetate. Organic layer was washed with saturated aqueous sodium hydrogen carbonate solution and dried over anhydrous sodium sulfate. After removing anhydrous sodium sulfate by filtration, the filtrate was concentrated. The residue was purified by thin layer chromatography (silica gel, mobile phase: hexane/ethyl acetate=1/2) to obtain (E)-2-(2-chloro-6-fluorobenzamido)-5-[4-(methyl-pyrimidin-2-ylamino)phenyl]pent-4-enoic acid methyl ester (39 mg).

Aufarbeitung

  1. extractionthe resulting mixture was extracted with ethyl acetate
  2. washOrganic layer was washed with saturated aqueous sodium hydrogen carbonate solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. customAfter removing anhydrous sodium sulfate
  5. filtrationby filtration
  6. concentrationthe filtrate was concentrated
  7. customThe residue was purified by thin layer chromatography (silica gel, mobile phase: hexane/ethyl acetate=1/2)

Quellen und Nachweise

ORD-Eintrag
ord-441d8f3842bd4d9383d7493200f2f449
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07566724B2

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