Methyl 6-amino-5-chloronicotinate → Methyl 6-amino-5-chloronicotinate

HRID 872308Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 872308
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[C:8]([Cl:10])[C:7]([NH2:11])=[N:6][CH:5]=1.[C:13]([O:17][C:18](=[O:40])[NH:19][C:20]1([C:24]2[CH:29]=[CH:28][C:27]([C:30](=O)[CH:31](Br)[C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)=[CH:26][CH:25]=2)[CH2:23][CH2:22][CH2:21]1)([CH3:16])([CH3:15])[CH3:14]>C(O)(C)C.C(Cl)Cl.O>[CH3:1][O:2][C:3]([C:4]1[CH:9]=[C:8]([Cl:10])[C:7]2[N:6]([C:31]([C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)=[C:30]([C:27]3[CH:26]=[CH:25][C:24]([C:20]4([NH:19][C:18]([O:17][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:40])[CH2:23][CH2:22][CH2:21]4)=[CH:29][CH:28]=3)[N:11]=2)[CH:5]=1)=[O:12].[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[C:8]([Cl:10])[C:7]([NH2:11])=[N:6][CH:5]=1

Komponenten

7

Edukt 2

HCID 45594319Methyl 6-amino-5-chloronicotinateHCID 86691038tert-Butyl (1-{4-[bromo(phenyl)acetyl]phenyl}cyclobutyl)carbamate

Produkt 2

HCID 45594319Methyl 6-amino-5-chloronicotinateHCID 66665474HCID 66665474, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 3776IsopropanolLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of 6-amino-5-chloronicotinic acid methyl ester (0.588 g, 3.15 mmol), {1-[4-(2-bromo-2-phenyl-acetyl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester [Int-1-A] (2.00 g, 70% purity by UPLC-MS, 3.15 mmol) and powdered activated 3 Å molecular sieves in isopropanol (9.7 mL) was heated at reflux for 20 hours. On cooling, the mixture was diluted with DCM and water, filtered through Celite and the organic extract washed with brine, dried and concentrated in vacuo. Purification was achieved by chromatography on silica gel (gradient elution: hexane-hexane/ethyl acetate 1:1) to give the title compound contaminated with 6-amino-5-chloronicotinic acid methyl ester. Further purification was achieved by acid extraction of a solution of the crude product in ethyl acetate with dilute aqueous hydrochloric acid (1 M). The organic extract was washed with brine, dried and concentrated in vacuo to give the title compound;

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for 20 hours
  3. temperatureOn cooling
  4. filtrationfiltered through Celite
  5. extractionthe organic extract
  6. washwashed with brine
  7. customdried
  8. concentrationconcentrated in vacuo
  9. customPurification

Quellen und Nachweise

ORD-Eintrag
ord-ef580607d65340f7b466f50e75715fce
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08975265B2

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