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5-methanesulfonyl-1-methyl-1H-1,2,3,4-tetrazole → 2-(2,6-Diethylphenyl)-4-methyl-6-(1-methyl-1H-tetrazol-5-yl)-5,6,7,8-tetrahydro-1,6-naphthyridine

HRID 80828
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 80828
Cl.Cl.[CH2:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH2:11][CH3:12])[C:6]=1[C:13]1[CH:22]=[C:21]([CH3:23])[C:20]2[CH2:19][NH:18][CH2:17][CH2:16][C:15]=2[N:14]=1)[CH3:4].[CH3:24][N:25]1[C:29](S(C)(=O)=O)=[N:28][N:27]=[N:26]1>C1COCC1.[Li]CCCC.[Cl-].[Na+].O.CCOC(C)=O>[CH2:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH2:11][CH3:12])[C:6]=1[C:13]1[CH:22]=[C:21]([CH3:23])[C:20]2[CH2:19][N:18]([C:29]3[N:25]([CH3:24])[N:26]=[N:27][N:28]=3)[CH2:17][CH2:16][C:15]=2[N:14]=1)[CH3:4]
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Komponenten

7

Edukt 2

HCID 64212595-methanesulfonyl-1-methyl-1H-1,2,3,4-tetrazoleHCID 86690277HCID 86690277, Verbindung

Produkt 1

HCID 712404722-(2,6-Diethylphenyl)-4-methyl-6-(1-methyl-1H-tetrazol-5-yl)-5,6,7,8-tetrahydro-1,6-naphthyridine

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel
HCID 57417360Sodium chloride; waterLösungsmittel
HCID 178418339ButyllithiumLösungsmittel

Versuchsvorschrift

To a solution of 2-(2,6-diethylphenyl)-4-methyl-5,6,7,8-tetrahydro-1,6-naphthyridine dihydrochloride (21.7 mg, 0.061 mmol) in THF (0.5 mL), 1.6 M n-BuLi in hexanes (0.119 mL, 0.190 mmol) was added at −78° C. under nitrogen. After stirring for 10 min. at the same temperature, 1-methyl-5-(methylsulfonyl)-1H-tetrazole (24.90 mg, 0.154 mmol) was added. The mixture was warmed up to rt and stirred for 19 h. The mixture was diluted with brine and EtOAc. The products were extracted with EtOAc, and the organic layer was concentrated. The crude was purified by RP-HPLC (X-Bridge Phenyl®, H2O (0.1% NH4OH)/CH3CN), then the fractions including the desired product were lyophilized to give the desired product. 1H NMR (400 MHz, CDCl3) δ ppm 7.26-7.30 (m, 2 H), 7.14 (d, J=7.58 Hz, 1 H), 6.98 (s, 1 H), 4.58 (s, 2 H), 4.01 (s, 3 H), 3.68 (t, J=5.94 Hz, 2 H), 3.25 (br t, J=5.94 Hz, 2 H), 2.30-2.37 (m, 7 H), 1.06 (t, J=7.58 Hz, 6 H); MS (ESI+) m/z 363.27 (M+H)+.

Aufarbeitung

  1. additionwas added
  2. extractionThe products were extracted with EtOAc
  3. concentrationthe organic layer was concentrated
  4. customThe crude was purified by RP-HPLC (X-Bridge Phenyl®, H2O (0.1% NH4OH)/CH3CN)

Quellen und Nachweise

ORD-Eintrag
ord-d8a04dedffa740b591448921b5b0c1d4
Quelldatensatz
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08846656B2

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