1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 131726935, Verbindung

HRID 133063

Reaktionsgleichung

Reaktionsgleichung von HRID 133063
[F:1][C:2]([F:13])([F:12])[C:3]1[N:11]=[C:6]2[CH2:7][NH:8][CH2:9][CH2:10][N:5]2[N:4]=1.[C:14]([O:18][C:19]([NH:21][C@H:22]([CH2:27][C:28]1[CH:33]=[C:32]([F:34])[C:31]([F:35])=[CH:30][C:29]=1[F:36])[CH2:23][C:24](O)=[O:25])=[O:20])([CH3:17])([CH3:16])[CH3:15].OC1C2N=NNC=2C=CC=1.Cl.CN(C)CCCN=C=NCC>CN(C=O)C>[C:14]([O:18][C:19]([NH:21][C@H:22]([CH2:27][C:28]1[CH:33]=[C:32]([F:34])[C:31]([F:35])=[CH:30][C:29]=1[F:36])[CH2:23][C:24]([N:8]1[CH2:9][CH2:10][N:5]2[N:4]=[C:3]([C:2]([F:12])([F:1])[F:13])[N:11]=[C:6]2[CH2:7]1)=[O:25])=[O:20])([CH3:17])([CH3:15])[CH3:16]

Komponenten

6

Edukt 4

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 7146288(R)-3-(tert-butoxycarbonylamino)-4-(2,4,5-trifluorophenyl)butanoic acid2×HCID 341763292-(Trifluoromethyl)-5,6,7,8-tetrahydro[1,2,4]triazolo[1,5-a]pyrazineHCID 178418300HCID 178418300, Verbindung

Produkt 1

HCID 131726935HCID 131726935, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 2-(trifluoromethyl)-5,6,7,8-tetrahydro[1,2,4]triazolo[1,5-α]pyrazine (28.8 mg, 0.15 mmol, from Step D) and (3R)-3-[(tert-butoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid (Intermediate 3, 50.0 mg, 0.15 mmol) in DMF (3 mL) was added hydroxybenzotriazole (HOBT, 26.1 mg, 0.19 mmol) at 0° C. The reaction was stirred at 0° C. for 5 min, then 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC, 37.0 mg, 0.19 mmol) was added. After removal of the ice-bath, the reaction was allowed to stir at ambient temperature for 16 h. After removal of the DMF by evaporation, the residue was partitioned between ethyl acetate and aqueous sodium bicarbonate. The aqueous layer was extracted three times with ethyl acetate. The combined organic layers were washed with brine and dried over magnesium sulfate. Concentration followed by preparative TLC (10% methanol/dichloromethane) gave the title compound as a foamy solid.

Aufarbeitung

  1. customAfter removal of the ice-bath
  2. stirringto stir at ambient temperature for 16 h
  3. customAfter removal of the DMF
  4. customby evaporation
  5. customthe residue was partitioned between ethyl acetate and aqueous sodium bicarbonate
  6. extractionThe aqueous layer was extracted three times with ethyl acetate
  7. washThe combined organic layers were washed with brine
  8. dry with materialdried over magnesium sulfate
  9. concentrationConcentration

Quellen und Nachweise

ORD-Eintrag
ord-b5e5f08436f8435b8fc276c0c2b74f5a
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07390809B2

Verknüpfte Notizen

Wird geladen…