4-Methylmorpholine → 2-(4-(benzyloxy)phenyl)-N-(1-(2-(pyrrolidin-1-yl)ethyl)-1H-indazol-6-yl)acetamide

HRID 1790124

Reaktionsgleichung

Reaktionsgleichung von HRID 1790124
[N:1]1([CH2:6][CH2:7][N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([NH2:17])[CH:15]=3)[CH:10]=[N:9]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:18]([O:25][C:26]1[CH:31]=[CH:30][C:29]([CH2:32][C:33](O)=[O:34])=[CH:28][CH:27]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.Cl.C(N=C=NC(C)(C)CC)C.ON1C2C=CC=CC=2N=N1.CN1CCOCC1>CN(C=O)C>[CH2:18]([O:25][C:26]1[CH:27]=[CH:28][C:29]([CH2:32][C:33]([NH:17][C:14]2[CH:15]=[C:16]3[C:11]([CH:10]=[N:9][N:8]3[CH2:7][CH2:6][N:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)=[CH:12][CH:13]=2)=[O:34])=[CH:30][CH:31]=1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Komponenten

7

Edukt 5

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 810334-Benzyloxyphenylacetic acidHCID 112762881-(2-Pyrrolidin-1-YL-ethyl)-1H-indazol-6-ylamineHCID 22992078Ethyldimethylpropylcarbodiimide hydrochloride

Produkt 1

HCID 117753992-(4-(benzyloxy)phenyl)-N-(1-(2-(pyrrolidin-1-yl)ethyl)-1H-indazol-6-yl)acetamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 1-(2-pyrrolidin-1-yl-ethyl)-1H-indazol-6-ylamine (48 mg, 0.21 mmol), (4-benzyloxy-phenyl)-acetic acid (50 mg, 0.21 mmol), ethyldimethylpropylcarbodiimide hydrochloride (47 mg g, 0.25 mmol), N-hydroxybenzotriazole (33 mg, 0.25 mmol), N-methyl morpholine (50 mg, 0.50 mmol) in 2 mL of DMF was shaken for 6 hours. The mixture was concentrated under reduced pressure, the residue was dissolved in 1.5 mL of a 1:1 mixture of dimethyl sulfoxide/methanol and purified by preparative reverse-phase HPLC. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.62 (m, 4H), 2.44 (m, 4H), 2.82 (t, 2H, J=6.78), 3.60 (s, 2H), 4.38 (t, 2H, J=6.78), 5.09 (s, 2H), 6.97 (m, 2H), 7.11–7.45 (m, 8H), 7.65 (m, 1H), 7.93 (m, 1H), 8.12 (s, 1H), 10.27 (s, 1H); MS (DCI/NH3) m/z 455 [M+H]+.

Aufarbeitung

  1. concentrationThe mixture was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in 1.5 mL of a 1:1 mixture of dimethyl sulfoxide/methanol
  3. custompurified by preparative reverse-phase HPLC

Quellen und Nachweise

ORD-Eintrag
ord-7df9f99af20b46018cd803d40e6ad47b
Quelldatensatz
uspto-grants-2006_07
Patentnummer
US07071182B2

Verknüpfte Notizen

Wird geladen…