Water → tert-Butyl 2-oxo-2-(4-(5-(3-phenoxy-5-(pyridin-2-ylthio)pyridin-2-ylamino)-1,2,4-thiadiazol-3-yl)piperidin-1-yl)ethylcarbamate

HRID 335167

Reaktionsgleichung

Reaktionsgleichung von HRID 335167
[O:1]([C:8]1[C:9]([NH:21][C:22]2[S:26][N:25]=[C:24]([CH:27]3[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]3)[N:23]=2)=[N:10][CH:11]=[C:12]([S:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)[CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:33]([O:37][C:38](CC(O)=O)=[O:39])([CH3:36])([CH3:35])[CH3:34].Cl.[CH2:45]([N:47]=C=NCCCN(C)C)[CH3:46].C(N(CC)CC)C.[OH2:63]>CN(C)C1C=CN=CC=1.C(Cl)Cl>[O:63]=[C:46]([N:30]1[CH2:31][CH2:32][CH:27]([C:24]2[N:23]=[C:22]([NH:21][C:9]3[C:8]([O:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)=[CH:13][C:12]([S:14][C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=4)=[CH:11][N:10]=3)[S:26][N:25]=2)[CH2:28][CH2:29]1)[CH2:45][NH:47][C:38](=[O:39])[O:37][C:33]([CH3:34])([CH3:35])[CH3:36]

Komponenten

8

Edukt 5

HCID 962WaterHCID 8471TriethylamineHCID 5458533-(Tert-butoxy)-3-oxopropanoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 577427923-Phenoxy-N-(3-(piperidin-4-yl)-1,2,4-thiadiazol-5-yl)-5-(pyridin-2-ylthio)pyridin-2-amine

Produkt 1

HCID 57742767tert-Butyl 2-oxo-2-(4-(5-(3-phenoxy-5-(pyridin-2-ylthio)pyridin-2-ylamino)-1,2,4-thiadiazol-3-yl)piperidin-1-yl)ethylcarbamateAusbeute 83,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

3-Phenoxy-N-(3-(piperidin-4-yl)-1,2,4-thiadiazol-5-yl)-5-(pyridin-2-ylthio)pyridin-2-amine (0.100 g, 0.2162 mmol), 2-(tert-butoxycarbonyl)acetic acid (0.04544 g, 0.2594 mmol), N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (0.06216 g, 0.3243 mmol), and N,N-dimethylpyridin-4-amine (0.002641 g, 0.02162 mmol) were dissolved in CH2Cl2 (5 mL). Triethylamine (0.04375 g, 0.4323 mmol) was added and the solution was stirred at ambient temperature for 3 hours. Water was added and the solution was extracted with CH2Cl2, dried, filtered, and concentrated. The residue was purified by silica gel (1-2% MeOH in CH2Cl2) to give the title compound (0.1116 g, 83.30% yield). 1H NMR (d6-DMSO) δ 12.35 (s, 1H), 8.39 (d, 1H), 8.37 (m, 1H), 7.66 (dt, 1H), 7.47 (d, 1H), 7.42 (t, 2H), 7.21-7.11 (m, 5H), 6.73 (t, 1H), 4.29 (t, 1H), 3.81 (m, 3H), 3.20-3.02 (m, 2H), 2.81 (t, 1H), 2.01 (m, 2H), 1.76-1.53 (m, 2H), 1.38 (s, 9H).

Aufarbeitung

  1. extractionthe solution was extracted with CH2Cl2
  2. customdried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel (1-2% MeOH in CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-af8c9fea69bd4e44b614fc86c8bd78c6
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08883828B2

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