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Diisopropylethylamine → [(S)-1-Methyl-2-(7-{[(pyridine-3-carbonyl)-amino]-methyl}-furo[2,3-g]indazol-1-yl)-ethyl]-carbamic acid benzyl ester

HRID 1453901
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1453901
[CH2:1]([O:8][C:9](=[O:28])[NH:10][C@@H:11]([CH3:27])[CH2:12][N:13]1[C:21]2[C:16](=[CH:17][CH:18]=[C:19]3[O:24][C:23]([CH2:25][NH2:26])=[CH:22][C:20]3=2)[CH:15]=[N:14]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.[C:38](Cl)(=[O:45])[C:39]1[CH:44]=[CH:43][CH:42]=[N:41][CH:40]=1>C1COCC1>[CH2:1]([O:8][C:9](=[O:28])[NH:10][C@@H:11]([CH3:27])[CH2:12][N:13]1[C:21]2[C:16](=[CH:17][CH:18]=[C:19]3[O:24][C:23]([CH2:25][NH:26][C:38]([C:39]4[CH:40]=[N:41][CH:42]=[CH:43][CH:44]=4)=[O:45])=[CH:22][C:20]3=2)[CH:15]=[N:14]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 82604Nicotinoyl chlorideHCID 68858114[(S)-2-(7-Aminomethyl-furo[2,3-g]indazol-1-yl)-1-methylethyl]-carbamic acid benzyl ester

Produkt 1

HCID 68857650[(S)-1-Methyl-2-(7-{[(pyridine-3-carbonyl)-amino]-methyl}-furo[2,3-g]indazol-1-yl)-ethyl]-carbamic acid benzyl esterAusbeute 39,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel

Versuchsvorschrift

To a solution of the product from Step B (0.32 g, 0.847 mmol) in THF (20 mL) was added polymer supported di-isopropyl ethyl amine (3.86 mmol/g, 0.44 g, 1.69 mmol, 2 eq); this suspension was cooled (ice bath) and nicotinoyl chloride (0.15 g, 0.847 mmol) was added. The ice bath was removed and mixture was stirred for one hour, additional nicotinoyl chloride (50 mg) was added and the mixture was stirred at room temperature overnight. Triethylamine was added and after stirring for 10 min saturated aqueous sodium bicarbonate (150 mL) was added. This mixture was extracted with ethyl acetate (2×100 mL). The combined extracts were dried (MgSO4) and evaporated to an oil which was purified by chromatography (silica gel, hexane/ethyl acetate gradient) to give a solid (0.16 g, 39%): LC/MS m/z 484 [M+H]+.

Aufarbeitung

  1. additionwas added
  2. customThe ice bath was removed
  3. additionadditional nicotinoyl chloride (50 mg) was added
  4. stirringthe mixture was stirred at room temperature overnight
  5. additionTriethylamine was added
  6. stirringafter stirring for 10 min saturated aqueous sodium bicarbonate (150 mL)
  7. additionwas added
  8. extractionThis mixture was extracted with ethyl acetate (2×100 mL)
  9. dry with materialThe combined extracts were dried (MgSO4)
  10. customevaporated to an oil which
  11. customwas purified by chromatography (silica gel, hexane/ethyl acetate gradient)

Quellen und Nachweise

ORD-Eintrag
ord-7eea3a321a924b429d94713b697d73d2
Quelldatensatz
uspto-grants-2009_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07476687B2

Notizen zur Reaktion

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