Sodium Carbonate → HCID 68602450, Verbindung

HRID 661669Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 661669
CCN=C=NCCCN(C)C.[Cl:12][C:13]1[CH:34]=[CH:33][C:16]([C:17]([N:19]([CH3:32])[C:20]2[CH:31]=[CH:30][CH:29]=[CH:28][C:21]=2[O:22][CH2:23][CH2:24][C:25](O)=[O:26])=[O:18])=[CH:15][C:14]=1[C:35]1[CH:36]=[N:37][C:38]([C:43]([F:46])([F:45])[F:44])=[CH:39][C:40]=1[C:41]#[N:42].[C:47]([O:51][C:52]([CH3:55])([CH3:54])[CH3:53])(=[O:50])[NH:48][NH2:49].C1C=CC2N(O)N=NC=2C=1.C([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C.ClCCl>[C:52]([O:51][C:47]([NH:48][NH:49][C:25](=[O:26])[CH2:24][CH2:23][O:22][C:21]1[CH:28]=[CH:29][CH:30]=[CH:31][C:20]=1[N:19]([C:17](=[O:18])[C:16]1[CH:33]=[CH:34][C:13]([Cl:12])=[C:14]([C:35]2[CH:36]=[N:37][C:38]([C:43]([F:44])([F:46])[F:45])=[CH:39][C:40]=2[C:41]#[N:42])[CH:15]=1)[CH3:32])=[O:50])([CH3:55])([CH3:54])[CH3:53]

Komponenten

8

Edukt 5

HCID 10340Sodium CarbonateHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 70091tert-Butyl carbazateHCID 757711-HydroxybenzotriazoleHCID 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

EDCI (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-31499f5ddff549789c30248af9dca1eb
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08084614B2

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