Triethylamine → n-[8-(4-Cyanonaphthalen-1-yl)-8-azabicyclo[3.2.1]oct-3-yl]-2-(ethoxyethoxy)acetamide

HRID 916358

Reaktionsgleichung

Reaktionsgleichung von HRID 916358
[CH2:1]([O:3][CH2:4][CH2:5][O:6][CH2:7][C:8]([OH:10])=O)[CH3:2].ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C.Cl.[NH2:29][CH:30]1[CH2:36][CH:35]2[N:37]([C:38]3[C:47]4[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=4)[C:41]([C:48]#[N:49])=[CH:40][CH:39]=3)[CH:32]([CH2:33][CH2:34]2)[CH2:31]1>CN(C=O)C>[C:48]([C:41]1[C:42]2[C:47](=[CH:46][CH:45]=[CH:44][CH:43]=2)[C:38]([N:37]2[CH:35]3[CH2:34][CH2:33][CH:32]2[CH2:31][CH:30]([NH:29][C:8](=[O:10])[CH2:7][O:6][CH2:5][CH2:4][O:3][CH2:1][CH3:2])[CH2:36]3)=[CH:39][CH:40]=1)#[N:49]

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 1928502-(2-Ethoxyethoxy)acetic acidHCID 1317266004-(3-Amino-8-azabicyclo[3.2.1]oct-8-yl)naphthalene-1-carbonitrile, hydrochloride

Produkt 1

HCID 69226204n-[8-(4-Cyanonaphthalen-1-yl)-8-azabicyclo[3.2.1]oct-3-yl]-2-(ethoxyethoxy)acetamideAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

165RL54 (19 mg, 0.13 mmol), O-benzotriazol-1-yl-N,N,N,N-tetramethyluronium tetrafluorophosphate (HBTU, 49 mg, 0.13 mmol), 1-hydroxybenzotriazole (18 mg, 0.13 mmol) and triethylamine (37 PL, 0.26 mmol) were dissolved in DMF (4 mL). 165RL21 (36 mg, 0.13 mmol)) was added and the mixture was shaken at rt for 30 min. The solvent was removed in vacuo and the product was purified by flash chromatography on silica gel using ethyl acetate/methanol (9:1) as eluent, giving the desired compound (38.1 mg, 72%).

Aufarbeitung

  1. customThe solvent was removed in vacuo
  2. customthe product was purified by flash chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-3cc8fde15b634778866eec076746e937
Quelldatensatz
uspto-grants-2007_09
Patentnummer
US07268232B2

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