1,2-Dichloroethane → 2-(Morpholin-4-yl)acetamide

HRID 1625366Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1625366
C(Cl)CCl.C1C=CC2N(O)N=[N:11]C=2C=1.[N:15]1([CH2:21][C:22]([OH:24])=O)[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1.C(N(CC)CC)C>CN(C=O)C>[N:15]1([CH2:21][C:22]([NH2:11])=[O:24])[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1

Komponenten

6

Edukt 4

HCID 111,2-Dichloroethane2×HCID 8471Triethylamine2×HCID 757711-Hydroxybenzotriazole2×HCID 4389684-Morpholineacetic acid2×

Produkt 1

HCID 6679102-(Morpholin-4-yl)acetamideAusbeute 108,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of [5-(3-amino-ethoxy)-1,3-dihydro-isoindol-2-yl]-(2,4-dihydroxy-5-isopropyl-phenyl)-methanone hydrochloride (100 mg, 0.255 mmoles) in DMF (10 ml) was added EDC (59 mg, 0.306 mmoles), HOBt (41 mg, 0.306 mmoles), morpholin-4-yl-acetic acid (37 mg, 0.255 mmoles) and triethylamine (43 μl, 0.306 mmoles) and stirred at ambient temperature for one hour. To the reaction mixture was added further EDC (20 mg, 0.104 mmoles), HOBt (14 mg, 0.104 mmoles), morpholin-4-yl-acetic acid (12 mg, 0.083 mmoles) and triethylamine (14 μl, 0.100 mmoles) and stirred at ambient temperature for a further 2 hours. Solvent removed in vacuo. The residue was purified by flash chromatography [Biotage SP4: 25S, flow rate 25 ml/min, gradient 20% DMAW 90 in DCM to 100% DMAW 90] and then by preparative HPLC to give N-{2-[2,4-dihydroxy-5-isopropyl-benzoyl)-2,3-dihydro-1H-isoindol-5-yloxy]-ethyl}-2-morpholin-4-yl-acetamide as a colourless viscous oil (40 mg, 33%). 1H NMR (Me-d3-OD) 7.20 (1H, br s); 7.18 (1H, s); 6.90 (2H, br m); 6.40 (1H, s); 4.10 (2H, t); 3.73 (4H, m); 3.63 (2H, t); 3.20 (1H, m); 3.18 (2H, s); 2.60 (4H, m); 1.25 (6H, d). MS: [M+H]+ 484.

Aufarbeitung

  1. stirringstirred at ambient temperature for a further 2 hours
  2. customSolvent removed in vacuo
  3. customThe residue was purified by flash chromatography [Biotage SP4: 25S, flow rate 25 ml/min, gradient 20% DMAW 90 in DCM to 100% DMAW 90]

Quellen und Nachweise

ORD-Eintrag
ord-0c86008a4211415089564be82b119dc5
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08779132B2

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