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Diisopropylethylamine → (E)-N-(3-Isopropyl-2-propoxybenzyl)-N-methyl-3-(7-oxo-5,6,7,8-tetrahydro-(1,8]naphthyridin-3-yl)acrylamide

HRID 1362285
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1362285
[CH:1]([C:4]1[C:5]([O:13][CH2:14][CH2:15][CH3:16])=[C:6]([CH:10]=[CH:11][CH:12]=1)[CH2:7]CN)([CH3:3])[CH3:2].[CH:17]([N:20](C(C)C)CC)(C)C.Cl.[O:27]=[C:28]1[NH:37][C:36]2[N:35]=[CH:34][C:33](/[CH:38]=[CH:39]/[C:40]([OH:42])=O)=[CH:32][C:31]=2[CH2:30][CH2:29]1.O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>CN(C=O)C.O>[CH:1]([C:4]1[C:5]([O:13][CH2:14][CH2:15][CH3:16])=[C:6]([CH:10]=[CH:11][CH:12]=1)[CH2:7][N:20]([CH3:17])[C:40](=[O:42])/[CH:39]=[CH:38]/[C:33]1[CH:34]=[N:35][C:36]2[NH:37][C:28](=[O:27])[CH2:29][CH2:30][C:31]=2[CH:32]=1)([CH3:2])[CH3:3]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 5

HCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 66905305(E)-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylic Acid HydrochlorideHCID 66966658(3-Isopropyl-2-propoxybenzyl)methylamine

Produkt 1

HCID 16662051
(E)-N-(3-Isopropyl-2-propoxybenzyl)-N-methyl-3-(7-oxo-5,6,7,8-tetrahydro-(1,8]naphthyridin-3-yl)acrylamide
Ausbeute 63 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of (3-isopropyl-2-propoxybenzyl)methylamine (0.238 g, 1.07 mmol) and diisopropyl-ethylamine (0.51 mL, 2.9 mmol) in DMF (20 mL) under N2 was treated sequentially with (E)-3-(7-oxo-5,6,7,8-tetrahydro-[1,8]naphthyridin-3-yl)acrylic acid hydrochloride (0.250 g, 0.981 mmol), 1-hydroxybenzotriazole hydrate (0.144 g, 1.07 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.205 g, 1.07 mmol). After stirring for 18 h, the reaction mixture was diluted with H2O (30 mL). The resulting solids were collected by filtration and when washed with Et2O (50 mL) were unexpectedly dissolved. The filtrate was extracted with EtOAc (3×50 mL). The combined organics were washed with brine (2×100 mL), dried (Na2SO4) and concentrated to a light yellow solid. Purification by column chromatography (silica gel, CH2Cl2/MeOH, 100 to 99.5:0.5) gave the title compound (0.26 g, 63%) as a white solid and as a mixture of amide rotamers: 1H NMR (500 MHz, DMSO-d6) δ 10.64-10.62 (m, 1H), 8.37-8.31 (m, 1H), 8.09-7.98 (m, 1H), 7.52-7.49 (m, 1H), 7.28-7.19 (m, 2H), 7.10-7.06 (m, 1H), 6.89-6.87 (m, 1H), 4.80-4.66 (m, 2H), 3.76-3.70 (m, 2H), 3.31-3.26 (m, 1H), 3.12-2.85 (m, 5H), 2.55-2.49 (m, 2H), 1.82-1.76 (m, 2H), 1.19-1.17 (m, 6H), 1.05-1.02 (m, 3H); MS (ESI) m/e 422 (M+H)+.

Aufarbeitung

  1. filtrationThe resulting solids were collected by filtration and when
  2. washwashed with Et2O (50 mL)
  3. dissolutionwere unexpectedly dissolved
  4. extractionThe filtrate was extracted with EtOAc (3×50 mL)
  5. washThe combined organics were washed with brine (2×100 mL)
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated to a light yellow solid
  8. customPurification by column chromatography (silica gel, CH2Cl2/MeOH, 100 to 99.5:0.5)

Quellen und Nachweise

ORD-Eintrag
ord-6bb9a41a7c6644919ea0f56ef1c3356a
Quelldatensatz
uspto-grants-2011_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07879872B2

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