1,2-Dichloroethane → N-Methyl-N-(3-methyl-benzofuran-2-ylmethyl)-3-(5,7,8,9-tetrahydro-6-oxa-1,9-diaza-benzocyclohepten-3-yl)-acrylamide

HRID 340832Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 340832
C(Cl)CCl.Cl.[N:6]1[C:11]2[NH:12][CH2:13][CH2:14][O:15][CH2:16][C:10]=2[CH:9]=[C:8]([C:17](=[CH2:21])C(O)=O)[CH:7]=1.C1C=CC2N([OH:31])N=NC=2C=1.CNC[C:35]1[O:36][C:37]2[CH:44]=[CH:43][CH:42]=[CH:41][C:38]=2[C:39]=1C.[CH2:45]([N:47]([CH:51](C)C)[CH:48]([CH3:50])C)C>CN(C=O)C.O>[CH3:51][N:47]([CH2:48][C:50]1[O:36][C:37]2[CH:44]=[CH:43][CH:42]=[CH:41][C:38]=2[C:39]=1[CH3:35])[C:45](=[O:31])[CH:21]=[CH:17][C:8]1[CH:7]=[N:6][C:11]2[NH:12][CH2:13][CH2:14][O:15][CH2:16][C:10]=2[CH:9]=1

Komponenten

8

Edukt 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 46785639N-methyl-1-(3-methylbenzofuran-2-yl)methanamineHCID 1317320875,7,8,9-Tetrahydro-6-oxa-1,9-diaza-benzocyclohepten-3-yl-acrylic acid hydrochloride

Produkt 1

HCID 68413589N-Methyl-N-(3-methyl-benzofuran-2-ylmethyl)-3-(5,7,8,9-tetrahydro-6-oxa-1,9-diaza-benzocyclohepten-3-yl)-acrylamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
35 °C

Versuchsvorschrift

EDC (0.10 g, 0.52 mmol) was added to a solution of 3-(5,7,8,9-Tetrahydro-6-oxa-1,9-diaza-benzocyclohepten-3-yl-acrylic acid hydrochloride (0.11 g, 0.43 mmol), HOBt (64 mg, 0.47 mmol), Methyl-(3-methyl-benzofuran-2-ylmethyl)-amine (91 mg, 0.52 mmol) and (i-Pr)2EtN (0.44 mL, 2.58 mmol) in DMF (6 mL). The mixture was allowed to stir overnight at 35° C. lire mixture was cooled to 0° C. and diluted with H2O (15 mL) with rapid stirring. The resulting precipitate was filtered, washed with H2O (30 mL) then dried under high vacuum. The solid was triturated with Et2O (3.0 mL), stirred for 20 mm then filtered to give a beige solid as a mixture of amide rotaruers. Yield: 0.10 g (62%); 1H NMR (300 MHz, DMSO-d6) δ8.25 (s, 1H), 7.94 (s, 1H), 7.59-7.03 (m, 6H), 6.79 (hr s, 1H), 4.98 and 4.79 (2×s, 2H), 4.53 (s, 2H), 3.77-3.73 (m, 2H), 3.25-3.19 (m, 2H), 3.17 and 2.93 (2×s, 3H), 2.28 (s, 3H); ESI MS m/z 378 [C22H23N3O3+H]+

Aufarbeitung

  1. temperaturewas cooled to 0° C.
  2. filtrationThe resulting precipitate was filtered
  3. washwashed with H2O (30 mL)
  4. customthen dried under high vacuum
  5. customThe solid was triturated with Et2O (3.0 mL)
  6. stirringstirred for 20 mm
  7. filtrationthen filtered
  8. customto give a beige solid

Quellen und Nachweise

ORD-Eintrag
ord-88e98d1462714e8cb54d5d2150daed46
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08895545B2

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