Triethylamine → HCID 178440809, Verbindung

HRID 534920Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 534920
Cl.Cl.[C:3]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1)([CH3:6])([CH3:5])[CH3:4].[NH:19]1[CH:23]=[N:22][C:21]([C:24](O)=[O:25])=[N:20]1.C(N(CC)CC)C.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>CN(C)C=O>[C:3]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N:13]1[CH2:18][CH2:17][N:16]([C:24]([C:21]2[N:22]=[CH:23][NH:19][N:20]=2)=[O:25])[CH2:15][CH2:14]1)([CH3:6])([CH3:4])[CH3:5]

Komponenten

7

Edukt 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 667511491-(2-Tert-butylphenyl)piperazine dihydrochlorideHCID 178524907HCID 178524907, Verbindung

Produkt 1

HCID 178440809HCID 178440809, VerbindungAusbeute 56 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 1-(2-tert-butylphenyl)piperazine dihydrochloride obtained in Reference Example 1 (0.30 g, 1.03 mmol), 1H-1,2,4-triazole-3-carboxylic acid (0.12 g, 1.08 mmol), triethylamine (0.22 g, 2.16 mmol), EDCI (0.21 g, 1.08 mmol) and HOBt (0.17 g, 1.08 mmol) in N,N-dimethylformamide (10 mL) was stirred at room temperature for 16 h. The reaction mixture was concentrated under reduced pressure and the resulting residue was partitioned between ethyl acetate and water, and the suspension of white precipitate in ethyl acetate was washed with 10% sodium hydrogen carbonate solution, water, saturated brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to afford white solid. This solid was triturated with diisopropyl ether to give the title compound (0.18 g, 56%) as a white solid, mp 295° C.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe resulting residue was partitioned between ethyl acetate and water
  3. additionthe suspension of white precipitate in ethyl acetate
  4. washwas washed with 10% sodium hydrogen carbonate solution, water, saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto afford white solid
  9. customThis solid was triturated with diisopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-043e597f8a054b728e3841ca70a53253
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08853215B2

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