Water → Methyl 4-[2-(3-dimethylaminobenzofuran-2-ylcarbonylamino)ethoxy]benzoate

HRID 1625281Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1625281
CN(C[C:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[O:7][C:6]=1[C:14]([OH:16])=O)C.CCN=C=NCCC[N:25]([CH3:27])[CH3:26].Cl.[CH:29]1[CH:30]=[CH:31][C:32]2N(O)N=N[C:33]=2[CH:34]=1.[OH2:39].[CH2:40]([N:42](CC)CC)[CH3:41].C[CH2:48][O:49][C:50](C)=[O:51]>CN(C=O)C>[CH3:27][N:25]([CH3:26])[C:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[O:7][C:6]=1[C:14]([NH:42][CH2:40][CH2:41][O:39][C:29]1[CH:30]=[CH:31][C:32]([C:50]([O:49][CH3:48])=[O:51])=[CH:33][CH:34]=1)=[O:16]

Komponenten

8

Edukt 6

HCID 962WaterHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 289433393-[(Dimethylamino)methyl]-1-benzofuran-2-carboxylic acid

Produkt 1

HCID 66688396Methyl 4-[2-(3-dimethylaminobenzofuran-2-ylcarbonylamino)ethoxy]benzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To 3-dimethylaminomethylbenzofuran-2-carboxylic acid (140 mg, 0.56 mmol) was added EDC.HCl (150 mg, 0.784 mmol) and HOBt.H2O (114 mg, 0.84 mmol) in anhydrous DMF. The reaction mixture was stirred for 30.60 min., after which methyl-(4-(2-ethoxyamine))benzoate hydrochloric salt (130 Mg, 0.56 mmol) and triethylamine (94 μl 0.672 mmol) were added and the reaction was stirred overnight. The reaction mixture was diluted with EtOAc and washed twice with saturated NaHCO3 (aq.) and brine. The organic extract was concentrated in vacuo to give methyl 4-[2-(3-dimethylaminobenzofuran-2-ylcarbonylamino)ethoxy]benzoate, which was then used without further purification.

Aufarbeitung

  1. stirringthe reaction was stirred overnight
  2. washwashed twice with saturated NaHCO3 (aq.) and brine
  3. extractionThe organic extract
  4. concentrationwas concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-eb7b38d5fd8e40c8a132991939f0edfa
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08779171B2

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