Hydrogen Bromide → (R)-3-(1-aminoethyl)-N-(3-chlorophenyl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazol-6-amine

HRID 446911Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 446911
[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[S:13][C:12]3=[N:14][N:15]=[C:16]([C@H:17]([NH:19]C(=O)OCC4C=CC=CC=4)[CH3:18])[N:11]3[N:10]=2)[CH:5]=[CH:6][CH:7]=1.Br>C(O)(=O)C.O>[NH2:19][C@@H:17]([C:16]1[N:11]2[C:12]([S:13][C:9]([NH:8][C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=3)=[N:10]2)=[N:14][N:15]=1)[CH3:18]

Komponenten

5

Edukt 2

HCID 260Hydrogen BromideHCID 86642295(R)-benzyl 1-(6-(3-chlorophenylamino)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazol-3-yl)ethylcarbamate

Produkt 1

HCID 59363289(R)-3-(1-aminoethyl)-N-(3-chlorophenyl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazol-6-amineAusbeute 70,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

(Step 8-iii) To a slurry of (R)-benzyl 1-(6-(3-chlorophenylamino)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazol-3-yl)ethylcarbamate (0.39 g, 0.92 mmol) in acetic acid (20 mL) was added 48% hydrobromic acid in water (10 mL). The mixture was heated to 90° C. for 2 hours. After cooling to room temperature, the resulting solution was concentrated to ⅓ the original volume, poured on ice and the pH adjusted to 8 with 2N sodium hydroxide. The resulting precipitate was filtered, washed with water, and dried overnight in vacuo to provide (R)-3-(1-aminoethyl)-N-(3-chlorophenyl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazol-6-amine (0.19 g): ESMS MH+=294.

Aufarbeitung

  1. temperatureAfter cooling to room temperature
  2. concentrationthe resulting solution was concentrated
  3. additionpoured on ice
  4. filtrationThe resulting precipitate was filtered
  5. washwashed with water
  6. customdried overnight in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-6446ea2ea20d4ac58d1082da7b13e87c
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08481538B2

Notizen zur Reaktion

Wird geladen…