4-Hydroxymethylpyridine → (1-{4-[3-Chloro-4-(pyridin-4-ylmethoxy)-phenylamino]-pyrrolo[2,1-f][1,2,4]triazin-5-ylmethyl}-piperidin-4-yl)-carbamic acid, tert-butyl ester

HRID 1829936Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1829936
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:15]3=[C:16]([CH2:19][N:20]4[CH2:25][CH2:24][CH:23]([NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])[CH2:22][CH2:21]4)[CH:17]=[CH:18][N:14]3[N:13]=[CH:12][N:11]=2)[CH:5]=[CH:6][C:7]=1[OH:8].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[CH2:54][C:55]1[CH:60]=[CH:59][N:58]=[CH:57][CH:56]=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:15]3=[C:16]([CH2:19][N:20]4[CH2:21][CH2:22][CH:23]([NH:26][C:27](=[O:33])[O:28][C:29]([CH3:30])([CH3:32])[CH3:31])[CH2:24][CH2:25]4)[CH:17]=[CH:18][N:14]3[N:13]=[CH:12][N:11]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:54][C:55]1[CH:60]=[CH:59][N:58]=[CH:57][CH:56]=1

Komponenten

6

Edukt 4

HCID 114724-HydroxymethylpyridineHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 21031521{1-[4-(3-Chloro-4-hydroxy-phenylamino)-pyrrolo[2,1-f][1,2,4]triazin-5-ylmethyl]-piperidin-4-yl}-carbamic acid, tert-butyl ester

Produkt 1

HCID 21031526(1-{4-[3-Chloro-4-(pyridin-4-ylmethoxy)-phenylamino]-pyrrolo[2,1-f][1,2,4]triazin-5-ylmethyl}-piperidin-4-yl)-carbamic acid, tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a mixture of 21A (0.047 g, 0.1 mmol), triphenylphosphine (79 mg, 0.3 mmol), and 4-hydroxymethylpyridine (22 mg, 0.2 mmol) in dry THF was added diethyl azodicarboxylate (0.047 ml, 0.3 mmol). The mixture was stirred at room temperature overnight and purified by preparative HPLC to give Compound 21B as a colorless semi-solid (TFA salt). Analytical HPLC retention time=2.303 min. (Chromolith Speed ROD column 4.6×50 mm, 10–90% aqueous methanol over 4 minutes containing 0.2% trifluoroacetic acid, 4 mL/min, monitoring at 254 nm) and a LC/MS M++1=564+.

Aufarbeitung

  1. custompurified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-ae2ab1793b4945ae928e5cc8d4c1948c
Quelldatensatz
uspto-grants-2006_06
Patentnummer
US07064203B2

Notizen zur Reaktion

Wird geladen…