Sodium Carbonate → HCID 68602450, Verbindung

HRID 448916Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 448916
CCN=C=NCCCN(C)C.Cl.[Cl:13][C:14]1[CH:35]=[CH:34][C:17]([C:18]([N:20]([CH3:33])[C:21]2[CH:32]=[CH:31][CH:30]=[CH:29][C:22]=2[O:23][CH2:24][CH2:25][C:26](O)=[O:27])=[O:19])=[CH:16][C:15]=1[C:36]1[CH:37]=[N:38][C:39]([C:44]([F:47])([F:46])[F:45])=[CH:40][C:41]=1[C:42]#[N:43].[C:48]([O:52][C:53]([CH3:56])([CH3:55])[CH3:54])(=[O:51])[NH:49][NH2:50].C1C=CC2N(O)N=NC=2C=1.C([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C.ClCCl>[C:53]([O:52][C:48]([NH:49][NH:50][C:26](=[O:27])[CH2:25][CH2:24][O:23][C:22]1[CH:29]=[CH:30][CH:31]=[CH:32][C:21]=1[N:20]([C:18](=[O:19])[C:17]1[CH:34]=[CH:35][C:14]([Cl:13])=[C:15]([C:36]2[CH:37]=[N:38][C:39]([C:44]([F:45])([F:47])[F:46])=[CH:40][C:41]=2[C:42]#[N:43])[CH:16]=1)[CH3:33])=[O:51])([CH3:56])([CH3:55])[CH3:54]

Komponenten

8

Edukt 5

HCID 10340Sodium CarbonateHCID 70091tert-Butyl carbazateHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 251587413-(2-{[4-Chloro-3-(4-cyano-6-trifluoromethyl-pyridin-3-yl)-benzoyl]-methyl-amino}-phenoxy)-propionic acid

Produkt 1

HCID 68602450HCID 68602450, VerbindungAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

EDCl (19.9 mg, 0.104 mmol) was added to a solution of 3-(2-{[4-chloro-3-(4-cyano-6-trifluoromethyl-pyridin-3-yl)-benzoyl]-methyl-amino}-phenoxy)-propionic acid 11-4 (36.3 mg, 0.069 mmol), t-butyl carbazate (13.7 mg, 0.104 mmol), HOBt (14.0 mg, 0.104 mmol) and Na2CO3 (8.7 mg, 0.104 mmol) in a mixture of DMF (1 mL) and dichloromethane (4 mL). The mixture was stirred at room temperature for approximately 16 hrs and was partitioned between ethyl acetate and water. The ethyl acetate layer was separated, washed with water and brine, and was dried over MgSO4. The organic filtrate was evaporated and purified by prep. TLC plate eluted with hexane and ethyl acetate (1/1) to yield N′-[3-(2-{[4-chloro-3-(4-cyano-6-trifluoromethyl-pyridin-3-yl)-benzoyl]-methyl-amino}-phenoxy)-propionyl]-hydrazinecarboxylic acid tert-butyl ester (40.1 mg, 94%). MS [M+H]+: 619.0; tR=2.40 min. (method 1)

Aufarbeitung

  1. customwas partitioned between ethyl acetate and water
  2. customThe ethyl acetate layer was separated
  3. washwashed with water and brine
  4. dry with materialwas dried over MgSO4
  5. customThe organic filtrate was evaporated
  6. custompurified by prep
  7. washTLC plate eluted with hexane and ethyl acetate (1/1)

Quellen und Nachweise

ORD-Eintrag
ord-c4dd244eca6d4c2db18649e851997586
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08481738B2

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