Dibutyltin oxide → 8-(5-(2H-tetrazol-5-yl)pentyloxy)-4-(3,5-dichloropyridin-4-ylamino)-7-methoxy-2H-chromen-2-one

HRID 20684

Reaktionsgleichung

[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:30])[C:7]=1[NH:8][C:9]1[C:18]2[C:13](=[C:14]([O:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][C:27]#[N:28])[C:15]([O:19][CH3:20])=[CH:16][CH:17]=2)[O:12][C:11](=[O:29])[CH:10]=1.C([Sn](=O)CCCC)CCC.[Si]([N:45]=[N+:46]=[N-:47])(C)(C)C>C1(C)C=CC=CC=1>[N:28]1[NH:45][N:46]=[N:47][C:27]=1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][O:21][C:14]1[C:15]([O:19][CH3:20])=[CH:16][CH:17]=[C:18]2[C:13]=1[O:12][C:11](=[O:29])[CH:10]=[C:9]2[NH:8][C:7]1[C:6]([Cl:30])=[CH:5][N:4]=[CH:3][C:2]=1[Cl:1]

Komponenten

Reaktionsbedingungen

Temperatur: 110 °C

Versuchsvorschrift

A mixture of 6-(4-(3,5-dichloropyridin-4-ylamino)-7-methoxy-2-oxo-2H-chromen-8-yloxy)hexanenitrile (170 mg, 0.38 mmol, Example 57), dibutyltin oxide (100 mg, 0.4 mmol), TMSN3 (0.5 mL, 3.8 mmol), and anhydrous toluene (5 mL) was heated at 110° C. under N2 for 15.5 h, allowed to cool to rt, and then quenched with methanol (1 mL). The reaction was concentrated and purified by silica gel chromatography (1:0→4:1; dichloromethane:methanol) to give 8-(5-(2H-tetrazol-5-yl)pentyloxy)-4-(3,5-dichloropyridin-4-ylamino)-7-methoxy-2H-chromen-2-one: 1H NMR (400 MHz, DMSO-d6): δ 9.51 (br s, 1H), 8.81 (s, 2H), 7.94 (d, 1H), 7.20 (d, 1H), 4.63 (s, 1H), 3.98 (t, 2H), 3.90 (s, 3H), 2.89 (t, 2H), 1.80-1.65 (m, 4H), 1.51 (m, 2H); MS (ESI): 490.9.

Aufarbeitung

temperatureto cool to rt
customquenched with methanol (1 mL)
concentrationThe reaction was concentrated
custompurified by silica gel chromatography (1:0→4:1; dichloromethane:methanol)

Quellen und Nachweise

ORD-Eintrag: ord-a0592a550548438085d588f39419403e
Quelldatensatz: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07745646B2

Verknüpfte Notizen

Wird geladen…