Ethylamine → N5-Ethyl-2-(6-{[(ethylamino)carbonyl]amino}pyridin-3-yl)-N4,N4-dimethyl-1,3-thiazole-4,5-dicarboxamide

HRID 2243028Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2243028
[CH3:1][N:2]([CH3:25])[C:3]([C:5]1[N:6]=[C:7]([C:13]2[CH:14]=[N:15][C:16]([NH:19][C:20]([NH:22][CH2:23][CH3:24])=[O:21])=[CH:17][CH:18]=2)[S:8][C:9]=1[C:10]([OH:12])=O)=[O:4].C1C=C[C:29]2N(O)N=[N:32][C:30]=2C=1.CN1CCOCC1.CCN=C=NCCCN(C)C.Cl.C(N)C>CN(C)C=O.C(OCC)(=O)C>[CH2:30]([NH:32][C:10]([C:9]1[S:8][C:7]([C:13]2[CH:14]=[N:15][C:16]([NH:19][C:20]([NH:22][CH2:23][CH3:24])=[O:21])=[CH:17][CH:18]=2)=[N:6][C:5]=1[C:3]([N:2]([CH3:1])[CH3:25])=[O:4])=[O:12])[CH3:29]

Komponenten

8

Edukt 5

HCID 6341EthylamineHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 592084804-[(Dimethylamino)carbonyl]-2-(6-{[(ethylamino)carbonyl]amino}pyridin-3-yl)-1,3-thiazole-5-carboxylic acid

Produkt 1

HCID 59208457N5-Ethyl-2-(6-{[(ethylamino)carbonyl]amino}pyridin-3-yl)-N4,N4-dimethyl-1,3-thiazole-4,5-dicarboxamideAusbeute 20 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a stirred solution of 4-[(dimethylamino)carbonyl]-2-(6-{[(ethylamino)carbonyl]amino}pyridin-3-yl)-1,3-thiazole-5-carboxylic acid (Example 53, 0.12 g, 3.3 mmol) in dry dimethylformamide (2 mL), HOBT (0.101 g, 6.6 mmol), N-methylmorpholine (0.108 mL, 9.9 mmol), EDC hydrochloride (0.126 g, 6.6 mmol), ethylamine (2 M in tetrahydrofuran, 0.13 mL, 3.3 mmol) were added at 0° C. and stirred overnight at room temperature. After completion of the reaction, reaction mixture was diluted with ethyl acetate (20 mL) and was washed with water (1×20 mL), 2 N hydrochloric acid (1×20 mL), and sodium bicarbonate solution (1×20 mL). The organic layer was dried, concentrated under reduced pressure and the residue was triturated with acetonitrile (1 mL). The obtained solid was filtered and dried to afford 0.018 g (20%) of the title compound as white solid. MS (APCI): 391 (M+H+) for C18H23N5O3S; NMR: δ 1.06 (t, 3H), 2.86 (s, 3H), 2.99 (s, 3H), 3.17 (q, 4H), 7.60 (d, 1H), 7.76 (br s, 1H), 8.22 (dd, 1H), 8.72 (br t, 1H), 8.78 (s, 1H), 9.52 (br s, 1H).

Aufarbeitung

  1. customAfter completion of the reaction, reaction mixture
  2. washwas washed with water (1×20 mL), 2 N hydrochloric acid (1×20 mL), and sodium bicarbonate solution (1×20 mL)
  3. customThe organic layer was dried
  4. concentrationconcentrated under reduced pressure
  5. customthe residue was triturated with acetonitrile (1 mL)
  6. filtrationThe obtained solid was filtered
  7. customdried

Quellen und Nachweise

ORD-Eintrag
ord-13ad2c0aae0349e599015cdf789f633a
Quelldatensatz
uspto-grants-2010_03
Patentnummer
US07674801B2

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