Acetic Acid → N-((2-(7-(2-Fluoro-4-nitrophenoxy)thieno[3,2-b]pyridin-2-yl)-1-methyl-1H-imidazol-5-yl)methyl)-2-methoxyethanamine

HRID 1026793Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1026793
[F:1][C:2]1[CH:25]=[C:24]([N+:26]([O-:28])=[O:27])[CH:23]=[CH:22][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[CH:11]=[C:12]([C:14]3[N:15]([CH3:21])[C:16]([CH:19]=O)=[CH:17][N:18]=3)[S:13][C:6]=12.[CH3:29][O:30][CH2:31][CH2:32][NH2:33].C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[F:1][C:2]1[CH:25]=[C:24]([N+:26]([O-:28])=[O:27])[CH:23]=[CH:22][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[CH:11]=[C:12]([C:14]3[N:15]([CH3:21])[C:16]([CH2:19][NH:33][CH2:32][CH2:31][O:30][CH3:29])=[CH:17][N:18]=3)[S:13][C:6]=12

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 80182-MethoxyethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 579195642-(7-(2-Fluoro-4-nitrophenoxy)thieno[3,2-b]pyridin-2-yl)-1-methyl-1H-imidazole-5-carbaldehyde

Produkt 1

HCID 57919595N-((2-(7-(2-Fluoro-4-nitrophenoxy)thieno[3,2-b]pyridin-2-yl)-1-methyl-1H-imidazol-5-yl)methyl)-2-methoxyethanamineAusbeute 100,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a suspension of 43 (1.3 g, 3.26 mmol) in dry DCM (50 mL) at RT was added 2-methoxyethanamine (1.226 g, 16.32 mmol), acetic acid (0.98 g, 16.32 mmol) and sodium triacetoxyborohydride (3.46 g, 16.32 mmol), and the reaction mixture was stirred at RT for 24 hours. It was then diluted with additional DCM and washed with saturated NaHCO3 solution, dried over Na2SO4, filtered and concentrated to dryness to afford 44 (1.5 g, 100% yield) as an yellow oil which was used crude in the next step with no additional purification. MS (m/z): 458.2 (M+H).

Aufarbeitung

  1. washwashed with saturated NaHCO3 solution
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-048e34849fe441389f1b4b6adc9711ec
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08729268B2

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