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Sodium bis(2-methoxyethoxy)aluminiumhydride → N-{4-[2-amino-6-{2-(cyclopropylmethoxy)-6-[(4-methoxybenzyl)oxy]phenyl}-3-(hydroxymethyl)-4-pyridinyl]-2-hydroxyphenyl}acetamide

HRID 2218269
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Reaktionsgleichung

Reaktionsgleichung von HRID 2218269
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:16]([C:17](OC(C)(C)C)=[O:18])=[C:15]([NH2:24])[N:14]=[C:13]([C:25]3[C:30]([O:31][CH2:32][C:33]4[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[CH:35][CH:34]=4)=[CH:29][CH:28]=[CH:27][C:26]=3[O:41][CH2:42][CH:43]3[CH2:45][CH2:44]3)[CH:12]=2)=[CH:7][C:6]=1[OH:46])(=[O:3])[CH3:2].[H-].COCCO[Al+]OCCOC.[Na+].[H-]>C1COCC1>[NH2:24][C:15]1[C:16]([CH2:17][OH:18])=[C:11]([C:8]2[CH:9]=[CH:10][C:5]([NH:4][C:1](=[O:3])[CH3:2])=[C:6]([OH:46])[CH:7]=2)[CH:12]=[C:13]([C:25]2[C:30]([O:31][CH2:32][C:33]3[CH:34]=[CH:35][C:36]([O:39][CH3:40])=[CH:37][CH:38]=3)=[CH:29][CH:28]=[CH:27][C:26]=2[O:41][CH2:42][CH:43]2[CH2:45][CH2:44]2)[N:14]=1
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Komponenten

4

Edukt 2

HCID 21584525Sodium bis(2-methoxyethoxy)aluminiumhydrideHCID 69147614HCID 69147614, Verbindung

Produkt 1

HCID 69144971N-{4-[2-amino-6-{2-(cyclopropylmethoxy)-6-[(4-methoxybenzyl)oxy]phenyl}-3-(hydroxymethyl)-4-pyridinyl]-2-hydroxyphenyl}acetamideAusbeute 33 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a cold (0° C.) solution of tert-butyl 4-[4-(acetylamino)-3-hydroxyphenyl]-2-amino-6-{2-(cyclopropylmethoxy)-6-[(4-methoxybenzyl)oxy]phenyl}nicotinate (1.65 g, 2.64 mmol) in THF (25.0 mL) under argon atmosphere was added a solution of sodium bis(2-methoxyethoxy)aluminum hydride (3.7 N in toluene, 4.12 mL, 21.1 mmol) in THF (3 mL) dropwise. After being stirred for 30 minutes, the mixture was quenched with ethyl acetate and poured into saturated aqueous sodium potassium tartarate. The extracted organic phase was washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (dichloromethane:methanol, 19:1-9:1) to give N-{4-[2-amino-6-{2-(cyclopropylmethoxy)-6-[(4-methoxybenzyl)oxy]phenyl}-3-(hydroxymethyl)-4-pyridinyl]-2-hydroxyphenyl}acetamide (0.48 g, 33%); LC-MS (m/z=556, M+1).

Aufarbeitung

  1. customthe mixture was quenched with ethyl acetate
  2. additionpoured into saturated aqueous sodium potassium tartarate
  3. washThe extracted organic phase was washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography on silica gel (dichloromethane:methanol, 19:1-9:1)

Quellen und Nachweise

ORD-Eintrag
ord-0d8e354ec74341b0b948feb5b6fd46a4
Quelldatensatz
uspto-grants-2008_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07410986B2

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