Hydrochloric Acid → (S)-2-methyl-1-(5-(5-(pyridin-2-ylthio)-3-(1,3,5-trimethyl-1H-pyrazol-4-yloxy)pyridin-2-ylamino)-1,2,4-thiadiazol-3-yl)propane-1,2-diol hydrochloride

HRID 1523653Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1523653
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[S:7][C:8]1[CH:9]=[C:10]([O:29][C:30]2[C:31]([CH3:37])=[N:32][N:33]([CH3:36])[C:34]=2[CH3:35])[C:11]([NH:14][C:15]2[S:19][N:18]=[C:17]([C@H:20]3[C:24]([CH3:26])([CH3:25])[O:23]C(C)(C)[O:21]3)[N:16]=2)=[N:12][CH:13]=1.[ClH:38]>C(O)C>[ClH:38].[CH3:26][C:24]([OH:23])([CH3:25])[C@H:20]([C:17]1[N:16]=[C:15]([NH:14][C:11]2[C:10]([O:29][C:30]3[C:31]([CH3:37])=[N:32][N:33]([CH3:36])[C:34]=3[CH3:35])=[CH:9][C:8]([S:7][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=3)=[CH:13][N:12]=2)[S:19][N:18]=1)[OH:21]

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 68473453(S)-N-(5-(pyridin-2-ylthio)-3-(1,3,5-trimethyl-1H-pyrazol-4-yloxy)pyridin-2-yl)-3-(2,2,5,5-tetramethyl-1,3-dioxolan-4-yl)-1,2,4-thiadiazol-5-amine

Produkt 1

HCID 67487906(S)-2-methyl-1-(5-(5-(pyridin-2-ylthio)-3-(1,3,5-trimethyl-1H-pyrazol-4-yloxy)pyridin-2-ylamino)-1,2,4-thiadiazol-3-yl)propane-1,2-diol hydrochlorideAusbeute 89,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

A flask was charged with (S)—N-(5-(pyridin-2-ylthio)-3-(1,3,5-trimethyl-1H-pyrazol-4-yloxy)pyridin-2-yl)-3-(2,2,5,5-tetramethyl-1,3-dioxolan-4-yl)-1,2,4-thiadiazol-5-amine (0.233 g, 0.432 mmol), ethanol (10 mL), and 3M HCl (0.288 ml, 0.863 mmol). The reaction was heated to 75° C. for 1 hour and then concentrated in vacuo. Ether was added to the residue and the mixture was stirred for 2 minutes to precipitate the product. The mixture was decanted and the resulting solids were dried in vacuo to afford (S)-2-methyl-1-(5-(5-(pyridin-2-ylthio)-3-(1,3,5-trimethyl-1H-pyrazol-4-yloxy)pyridin-2-ylamino)-1,2,4-thiadiazol-3-yl)propane-1,2-diol hydrochloride (0.248 g, 0.387 mmol, 89.6% yield) as yellow solid. Mass Spectrum (apci) m/z=500.1 (M+H−HCl).

Aufarbeitung

  1. concentrationconcentrated in vacuo
  2. additionEther was added to the residue
  3. customto precipitate the product
  4. customThe mixture was decanted
  5. customthe resulting solids were dried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-9346811e7c8a4fd099720a7ecf73e269
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09079890B2

Notizen zur Reaktion

Wird geladen…