Acetaldehyde → 6-Ethyl-2-(ethylamino)-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxamide

HRID 1483220

Reaktionsgleichung

Reaktionsgleichung von HRID 1483220
[NH2:1][C:2]1[S:12][C:5]2[CH2:6][N:7]([CH2:10][CH3:11])[CH2:8][CH2:9][C:4]=2[C:3]=1[C:13]([NH2:15])=[O:14].[CH:16](=O)[CH3:17].S([O-])([O-])(=O)=O.[Mg+2].C([BH3-])#N.[Na+]>C(O)(=O)C.CO.O1CCCC1>[CH2:10]([N:7]1[CH2:8][CH2:9][C:4]2[C:3]([C:13]([NH2:15])=[O:14])=[C:2]([NH:1][CH2:16][CH3:17])[S:12][C:5]=2[CH2:6]1)[CH3:11]

Komponenten

8

Edukt 4

HCID 177AcetaldehydeHCID 24083Sulfuric acid magnesium salt (1:1)HCID 6144392-Amino-6-ethyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxamideHCID 5003444Sodium cyanoborohydride

Produkt 1

HCID 680592166-Ethyl-2-(ethylamino)-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxamideAusbeute 80,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176Acetic AcidKatalysatorHCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred mixture of compound F4 (200 mg, 0.888 mmol), acetaldehyde (5 M in tetrahydrofuran, 0.360 mL, 1.80 mmol), acetic acid (two drops), anhydrous magnesium sulfate (200 mg) in anhydrous methanol (6 mL) and anhydrous tetrahydrofuran (3 mL) was added sodium cyanoborohydride (167 mg, 2.66 mmol) at room temperature under nitrogen. The reaction mixture was stirred for 23 h and then filtered. The filtrate was concentrated. The resulting residue was purified by flash column chromatography on silica gel eluting with 10% to 20% methanol/methylene chloride to afford compound R1 as a colourless syrup (181 mg, 80%): MS (M+H) 254.

Aufarbeitung

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated
  3. customThe resulting residue was purified by flash column chromatography on silica gel eluting with 10% to 20% methanol/methylene chloride

Quellen und Nachweise

ORD-Eintrag
ord-936824ed268141a19c4edc04c2fab9e6
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09416141B2

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