Diisopropylethylamine → HCID 18614392, Verbindung

HRID 1265175Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1265175
[CH2:1]=[C:2]1[CH2:6][CH2:5][C:4]([CH3:10])([C:7]([OH:9])=O)[CH2:3]1.Cl.[F:12][C:13]([F:27])([F:26])[C:14]1[CH:15]=[C:16]([CH:19]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:21]=1)[CH2:17]N.O[N:29]1C2N=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C.Cl.CN(C)CCCN=C=NCC>ClCCl>[F:12][C:13]([F:26])([F:27])[C:14]1[CH:15]=[C:16]([CH:19]=[C:20]([C:22]([F:25])([F:23])[F:24])[CH:21]=1)[CH2:17][CH:3]1[C:2](=[CH2:1])[CH2:6][CH2:5][C:4]1([CH3:10])[C:7]([NH2:29])=[O:9]

Komponenten

7

Edukt 5

HCID 81531DiisopropylethylamineHCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 186143561-[3,5-Bis(trifluoromethyl)phenyl]methanamine--hydrogen chloride (1/1)HCID 18614396400770-57-2

Produkt 1

HCID 18614392HCID 18614392, VerbindungAusbeute 49,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A solution of 3-methylene-1-methylcyclopentanecarboxylic acid, (600 mg, 4.28 mmol) 3,5-bis(trifluoromethyl)benzylamine hydrochloride (1.196 g, 4.28 mmol), 1-hydroxy-7-azabenzotriazole (583 mg, 4.28 mmol) and diisopropylethylamine (745 μL, 4.28 mmol) and 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (EDC, 1.230 g, 0.168, 6.42 mmol) in dichloromethane (10 mL) was stirred at room temperature for 1 hr. The reaction mixture was diluted with dichloromethane (40 mL) and washed with water (3×30 mL), brine (1×30 mL), dried (anhydrous sodium sulfate) and the solvent was evaporated under reduced pressure. The crude product was purified via mplc (Lobar Fertigsaule, LiChroprep, 40-63 μm, ethyl acetate/hexanes (1:4)) yielding 777.6 mg (49%) of pure product. 1H NMR (500 MHz, CDCl3) 7.79 (s, 1H), 7.70 (s, 2H), 6.19 (bs, 1H), 4.98 (bs, 1H), 4.92 (bs, 1H), 4.62 (dd, 15.6 Hz, 6.2 Hz, 1H), 4.54 (dd, 15.8 Hz, 6.0 Hz, 1H), 2.78 (bd, 15.8 Hz, 1H), 2.46 (m, 2H), 2.30 (bd, 15.8 Hz, 1H), 2.18 (m, 1H), 1.70 (m, 1H), 1.31 (s, 3H).

Aufarbeitung

  1. washwashed with water (3×30 mL), brine (1×30 mL)
  2. dry with materialdried (anhydrous sodium sulfate)
  3. customthe solvent was evaporated under reduced pressure
  4. customThe crude product was purified via mplc (Lobar Fertigsaule, LiChroprep, 40-63 μm, ethyl acetate/hexanes (1:4))

Quellen und Nachweise

ORD-Eintrag
ord-bfba64d9678f437680ae50832cf89f17
Quelldatensatz
uspto-grants-2003_04
Patentnummer
US06545023B2

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