1,2-Dichloroethane → 4-Amino-N-(1-azabicyclo[2.2.2]oct-3-yl)-3-iodobenzamide

HRID 2281181

Reaktionsgleichung

Reaktionsgleichung von HRID 2281181
Cl.Cl.[NH2:3][CH:4]1[CH:9]2[CH2:10][CH2:11][N:6]([CH2:7][CH2:8]2)[CH2:5]1.[NH2:12][C:13]1[CH:21]=[CH:20][C:16]([C:17](O)=[O:18])=[CH:15][C:14]=1[I:22].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.C(N(CC)C(C)C)(C)C>CN(C=O)C.O>[NH2:12][C:13]1[CH:21]=[CH:20][C:16]([C:17]([NH:3][CH:4]2[CH:9]3[CH2:10][CH2:11][N:6]([CH2:7][CH2:8]3)[CH2:5]2)=[O:18])=[CH:15][C:14]=1[I:22]

Komponenten

8

Edukt 5

HCID 111,2-DichloroethaneHCID 164614-Amino-3-iodobenzoic AcidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 197853Quinuclidine, 3-amino-, dihydrochloride

Produkt 1

HCID 589329434-Amino-N-(1-azabicyclo[2.2.2]oct-3-yl)-3-iodobenzamideAusbeute 90,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 2.04 g (10.3 mmol) of 3-aminoquinuclidine dihydrochloride, 2.70 g (10.3 mmol) of 4-amino-3-iodobenzoic acid, 1.39 g (10.3 mmol) of HOBt, 2.16 g (11.3 mmol) of EDC and 6.63 g (51.3 mmol) of N,N-diisopropylethylamine in 150 ml of DMF was stirred at room temperature for 16 h. 300 ml of water were added, and the aqueous phase was extracted three times with 300 ml of ethyl acetate each time. The combined organic phases were dried over sodium sulfate and the solvent was distilled off in vacuo. The residue was purified on a flash column (mobile phase: dichloromethane/methanol/triethylamine 90:10:0.2). 3.45 g (87%) of the desired title compound were obtained.

Aufarbeitung

  1. extractionthe aqueous phase was extracted three times with 300 ml of ethyl acetate each time
  2. dry with materialThe combined organic phases were dried over sodium sulfate
  3. distillationthe solvent was distilled off in vacuo
  4. customThe residue was purified on a flash column (mobile phase: dichloromethane/methanol/triethylamine 90:10:0.2)

Quellen und Nachweise

ORD-Eintrag
ord-bd76d74d0f2c406d8dcb04710c28358c
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09139579B2

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