Ammonium Chloride → 5-Amino-2-(6-morpholin-4-ylpyridin-3-yl)-1,3-thiazole-4-carboxamide

HRID 2060637Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2060637
[NH2:1][C:2]1[S:6][C:5]([C:7]2[CH:8]=[N:9][C:10]([N:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)=[CH:11][CH:12]=2)=[N:4][C:3]=1[C:19]([OH:21])=O.O[N:23]1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.[Cl-].[NH4+].C(N(C(C)C)CC)(C)C>CN(C)C=O>[NH2:1][C:2]1[S:6][C:5]([C:7]2[CH:8]=[N:9][C:10]([N:13]3[CH2:14][CH2:15][O:16][CH2:17][CH2:18]3)=[CH:11][CH:12]=2)=[N:4][C:3]=1[C:19]([NH2:23])=[O:21]

Komponenten

7

Edukt 5

HCID 25517Ammonium ChlorideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 583352705-Amino-2-(6-morpholin-4-ylpyridin-3-yl)-1,3-thiazole-4-carboxylic acid

Produkt 1

HCID 583352605-Amino-2-(6-morpholin-4-ylpyridin-3-yl)-1,3-thiazole-4-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

5-Amino-2-(6-morpholin-4-ylpyridin-3-yl)-1,3-thiazole-4-carboxylic acid (310 mg, 1.01 mmol), 1-hydroxybenzotriazole (310 mg, 2.02 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (388 mg, 2.02 mmol), and ammonium chloride (271 mg, 5.06 mmol) were taken up in dimethylformamide (20 mL) under argon. Diisopropylethylamine (0.88 mL, 5.06 mmol) was added and the mixture was stirred at ambient temperature for 36 hours. The mixture was then concentrated in vacuo. The resulting residue was purified via flash chromatography (silica, 0-10% methanol/ethyl acetate) to afford the title compound. LRMS (APCI) calc'd for (C13H16N5O2S) [M+H]+, 306.1; found 306.0.

Aufarbeitung

  1. concentrationThe mixture was then concentrated in vacuo
  2. customThe resulting residue was purified via flash chromatography (silica, 0-10% methanol/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-8e9955962ca244eb87852a38071c15ec
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08278335B2

Notizen zur Reaktion

Wird geladen…