1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → (E)-3-(2,2-Dimethyl-3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-7-yl)-N-(3-methoxy-2-propoxy-benzyl)-N-methyl-acrylamide

HRID 1362388Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1362388
[CH3:1][O:2][C:3]1[C:4]([O:12][CH2:13][CH2:14][CH3:15])=[C:5]([CH:9]=[CH:10][CH:11]=1)[CH2:6][NH:7][CH3:8].[CH3:16][C:17]1([CH3:33])[O:22][C:21]2[CH:23]=[C:24]([CH:27]=[CH:28][C:29]([OH:31])=O)[CH:25]=[N:26][C:20]=2[NH:19][C:18]1=[O:32].ON1C2C=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C.CN(C)CCCN=C=NCC>CN(C=O)C.O>[CH3:33][C:17]1([CH3:16])[O:22][C:21]2[CH:23]=[C:24](/[CH:27]=[CH:28]/[C:29]([N:7]([CH2:6][C:5]3[CH:9]=[CH:10][CH:11]=[C:3]([O:2][CH3:1])[C:4]=3[O:12][CH2:13][CH2:14][CH3:15])[CH3:8])=[O:31])[CH:25]=[N:26][C:20]=2[NH:19][C:18]1=[O:32]

Komponenten

8

Edukt 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 28338626(3-Methoxy-2-propoxybenzyl)methylamineHCID 669676363-(2,2-dimethyl-3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-7-yl)-acrylic acid

Produkt 1

HCID 16660813(E)-3-(2,2-Dimethyl-3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-7-yl)-N-(3-methoxy-2-propoxy-benzyl)-N-methyl-acrylamideAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of (3-methoxy-2-propoxy-benzyl)-methyl-amine (115 mg, 0.55 mmol) in DMF (5 mL) were added in sequential order 3-(2,2-dimethyl-3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-7-yl)-acrylic acid (181 mg, 0.5 mmol), 1-hydroxybenzotriazole (74 mg, 0.55 mmol), diisopropylethylamine (261 uL, 1.5 mmol), and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide (110 mg, 0.55 mmol). The reaction was placed in a microwave at 130° C. for 5 min. The solution was cooled in an ice bath and water was added with rapid stirring. The precipitate was filtered, dried and triturated with diethyl ether to yield the title compound (164 mg, 75%) as a white solid and as a mixture of amide rotomers: 1H NMR (400 MHz, DMSO-d6) δ 11.37-11.39 (m, 1H), 8.14-8.18 (m, 1H), 7.87-7.93 (m, 1H), 7.47-7.53 (m, 1H), 7.27-7.34 (m, 1H), 6.92-7.09 (m, 3H), 6.60-6.66 (m, 1H), 4.62-4.79 (m, 2H), 3.84-3.90 (m, 2H), 3.78 (s, 3H), 2.88-3.09 (m, 3H), 1.70-1.74 (m, 2H), 1.40-1.49 (m 6H), 0.93-0.99 (m, 3H); MS (ESI) m/e 440 (C24H29N3O5+H)+.

Aufarbeitung

  1. temperatureThe solution was cooled in an ice bath
  2. filtrationThe precipitate was filtered
  3. customdried
  4. customtriturated with diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-132ad0a903334d11a57cf1d8978cd754
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07879872B2

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