2-Amino-2,3-dimethylbutanamide → 5-[(1-Carbamoyl-1,2-dimethylpropyl)carbamoyl]3-chlorothieno[3,2-b]pyridine-6-carboxylic acid

HRID 365078Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 365078
[NH2:1][C:2]([CH3:9])([CH:6]([CH3:8])[CH3:7])[C:3]([NH2:5])=[O:4].[Cl:10][C:11]1[C:15]2=[N:16][C:17]3[C:23](=[O:24])[O:22][C:20](=[O:21])[C:18]=3[CH:19]=[C:14]2[S:13][CH:12]=1>C1COCC1>[C:3]([C:2]([NH:1][C:23]([C:17]1[N:16]=[C:15]2[C:11]([Cl:10])=[CH:12][S:13][C:14]2=[CH:19][C:18]=1[C:20]([OH:22])=[O:21])=[O:24])([CH3:9])[CH:6]([CH3:8])[CH3:7])(=[O:4])[NH2:5]

Komponenten

4

Edukt 2

HCID 97937732-Amino-2,3-dimethylbutanamideHCID 137524853-Chlorothieno[3,2-b]pyridine-5,6-dicarboxylic acid anhydride

Produkt 1

HCID 137525025-[(1-Carbamoyl-1,2-dimethylpropyl)carbamoyl]3-chlorothieno[3,2-b]pyridine-6-carboxylic acidAusbeute 75,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

2-Amino-2,3-dimethylbutyramide (0.71 g) all in one portion is added to a stirred solution of 3-chlorothieno[3,2-b]pyridine-5,6-dicarboxylic acid anhydride, (1.2 g) in THF (1.0 mL). After standing for five minutes, the ice bath is removed and the reaction stirred at room temperature for 28 hours. THF (5 mL) is added and the mixture heated at reflux for two hours and then set aside overnight. The cooled mixture is filtered and the collected solid washed with ether to give 1.4 g of the desired 5-[(1-carbamoyl-1,2-dimethylpropyl)carbamoyl]3-chlorothieno[3,2-b]pyridine-6-carboxylic acid.

Aufarbeitung

  1. customthe ice bath is removed
  2. additionTHF (5 mL) is added
  3. temperaturethe mixture heated
  4. temperatureat reflux for two hours
  5. waitset aside overnight
  6. filtrationThe cooled mixture is filtered
  7. washthe collected solid washed with ether

Quellen und Nachweise

ORD-Eintrag
ord-0269698e4f8849b7ad328d3b580ace77
Quelldatensatz
uspto-grants-1986_08
Patentnummer
US04608079

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