Triethylamine → (E)-3-(6-Amino-pyridin-3-yl)-N-methyl-N-thieno[3,2-c]pyridin-2-ylmethyl-acrylamide

HRID 1711921Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1711921
CCN=C=NCCCN(C)C.Cl.[CH3:13][NH:14][CH2:15][C:16]1[S:24][C:23]2[CH:22]=[CH:21][N:20]=[CH:19][C:18]=2[CH:17]=1.[NH2:25][C:26]1[N:31]=[CH:30][C:29]([CH:32]=[CH:33][C:34]([OH:36])=O)=[CH:28][CH:27]=1.C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C>CN(C=O)C.O>[NH2:25][C:26]1[N:31]=[CH:30][C:29](/[CH:32]=[CH:33]/[C:34]([N:14]([CH3:13])[CH2:15][C:16]2[S:24][C:23]3[CH:22]=[CH:21][N:20]=[CH:19][C:18]=3[CH:17]=2)=[O:36])=[CH:28][CH:27]=1

Komponenten

8

Edukt 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 45117642Methyl-thieno[3,2-c]pyridin-2-ylmethyl-amineHCID 534008323-(6-Aminopyridin-3-yl)prop-2-enoic acid

Produkt 1

HCID 66967013(E)-3-(6-Amino-pyridin-3-yl)-N-methyl-N-thieno[3,2-c]pyridin-2-ylmethyl-acrylamideAusbeute 61 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

EDC hydrochloride (118 mg, 0.62 mmol) was added to a solution of methyl-thieno[3,2-c]pyridine-2-ylmethyl-amine (100 mg, 0.56 mmol), (−3-(6-amino-pyridin-3-yl)acrylic acid (101 mg, 0.62 mmol), HOBt.H2O (83 mg, 0.62 mmol) and triethylamine (235 μL, 1.68 mmol) in anhydrous DMF (5 mL). The mixture was stirred at room temperature overnight then diluted with H2O (10 mL) and extracted with CH2Cl2 (3×50 mL). The combined organic fractions were dried over MgSO4, filtered and evaporated to give a yellow residue which was subjected to flash chromatography on silica gel (10% MeOH: CH2Cl2) to yield the title compound (61.0%). 1H-NMR (300 MHz, CDCl3) δ 9.04 (s, 1H), 8.45 (d, J=5.3 Hz, 1H), 8.26 (s, 1H), 7.76-7.67 (m, 3H), 7.32 (d, J=15.0 Hz, 1H), 6.76 (d, J=15.2 Hz, 1H), 6.53 (d, J=8.3 Hz, 1H), 4.95 (s, 2H), 4.76 (br s, 2H), 3.22 (s, 3M); MS (ES) m/e 325.1 (M+H)+.

Aufarbeitung

  1. extractionextracted with CH2Cl2 (3×50 mL)
  2. dry with materialThe combined organic fractions were dried over MgSO4
  3. filtrationfiltered
  4. customevaporated
  5. customto give a yellow residue which

Quellen und Nachweise

ORD-Eintrag
ord-e0ad788411514a629ccf0b898f0b74dc
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07790709B2

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