Ammonium Chloride → 5-{[6-(2-Hydroxy-1-morpholin-4-ylethyl)pyridin-2-yl]amino}-2-(6-morpholin-4-ylpyridin-3-yl)-1,3-thiazole-4-carboxamide

HRID 2060635Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2060635
[OH:1][CH2:2][CH:3]([C:10]1[N:15]=[C:14]([NH:16][C:17]2[S:21][C:20]([C:22]3[CH:23]=[N:24][C:25]([N:28]4[CH2:33][CH2:32][O:31][CH2:30][CH2:29]4)=[CH:26][CH:27]=3)=[N:19][C:18]=2[C:34]([OH:36])=O)[CH:13]=[CH:12][CH:11]=1)[N:4]1[CH2:9][CH2:8][O:7][CH2:6][CH2:5]1.O[N:38]1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.[Cl-].[NH4+].C(N(C(C)C)CC)(C)C>CN(C=O)C.O>[OH:1][CH2:2][CH:3]([C:10]1[N:15]=[C:14]([NH:16][C:17]2[S:21][C:20]([C:22]3[CH:23]=[N:24][C:25]([N:28]4[CH2:33][CH2:32][O:31][CH2:30][CH2:29]4)=[CH:26][CH:27]=3)=[N:19][C:18]=2[C:34]([NH2:38])=[O:36])[CH:13]=[CH:12][CH:11]=1)[N:4]1[CH2:9][CH2:8][O:7][CH2:6][CH2:5]1

Komponenten

8

Edukt 5

HCID 25517Ammonium ChlorideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 583352745-{[6-(2-Hydroxy-1-morpholin-4-ylethyl)pyridin-2-yl]amino}-2-(6-morpholin-4-ylpyridin-3-yl)-1,3-thiazole-4-carboxylic acid

Produkt 1

HCID 451019395-{[6-(2-Hydroxy-1-morpholin-4-ylethyl)pyridin-2-yl]amino}-2-(6-morpholin-4-ylpyridin-3-yl)-1,3-thiazole-4-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

5-{[6-(2-Hydroxy-1-morpholin-4-ylethyl)pyridin-2-yl]amino}-2-(6-morpholin-4-ylpyridin-3-yl)-1,3-thiazole-4-carboxylic acid (64 mg, 0.13 mmol), N-hydroxybenzotriazole (39 mg, 0.25 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (48 mg, 0.25 mmol), and ammonium chloride (34 mg, 0.63 mmol) were taken up in DMF (4.2 mL) under argon. Diisopropylethylamine (110 μl, 0.63 mmol) was added and the mixture was stirred at room temperature for 36 hours. The solution was then diluted with water to precipitate a white solid that was collected by filtration, washed with water and dried under reduced pressure to afford the title compound as a bright yellow solid. 1H NMR (500 MHz, d6-DMSO): δ 11.21 (s, 1H), 8.66 (d, 1H), 8.08 (dd, 1H), 7.72 (s, 1H), 7.69 (t, 1H), 7.59 (s, 1H), 7.05 (d, 1H), 6.96 (d, 1H), 6.93 (d, 1H), 4.53 (m, 1H), 3.99 (m, 2H), 3.69 (m, 5H), 3.55 (m, 8H), 2.50 (m, 4H). LRMS (APCI) calc'd for C24H30N7O4S [M+H]+ 512.2, found 512.1

Aufarbeitung

  1. customto precipitate a white solid
  2. filtrationthat was collected by filtration
  3. washwashed with water
  4. customdried under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-f8726849af1e49c8b287f8605402c63f
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08278335B2

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