Diisopropylethylamine → HCID 178488472, Verbindung

HRID 1669852Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1669852
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[N:13]([CH2:14][C:15]3[CH:23]=[CH:22][C:18]([C:19]([OH:21])=O)=[CH:17][CH:16]=3)[N:12]=[C:11]([C:24]3[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=3)[CH:10]=2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.O[N:33]1[C:37]2[N:38]=CC=C[C:36]=2[N:35]=[N:34]1.C([N:45](C(C)C)CC)(C)C.Cl.CN(C)CCCN=C=NCC>C(OCC)(=O)C.CN(C=O)C.C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[N:13]([CH2:14][C:15]3[CH:23]=[CH:22][C:18]([C:19]([NH:38][CH2:37][C:36]4[NH:45][N:33]=[N:34][N:35]=4)=[O:21])=[CH:17][CH:16]=3)[N:12]=[C:11]([C:24]3[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=3)[CH:10]=2)[CH:5]=[C:6]([Cl:8])[CH:7]=1

Komponenten

7

Edukt 4

HCID 81531DiisopropylethylamineHCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 67337219HCID 67337219, Verbindung

Produkt 1

HCID 178488472HCID 178488472, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8857Ethyl AcetateLösungsmittelHCID 22350042dichloromethane N,N-dimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of the intermediate from example 76 step A (100 mg, 0.22 mmol) in 1:1 DMF/DCM (0.54 mL) was added 1-hydroxy-7-azabenzo-triazole (35 mg, 0.264 mmol), NAN-diisopropylethyl amine (92 μL, 0.53 mmol) amino methyl tetrazole (26 mg, 0.26 mmol) and 1-(3-(Dimethylamino)propyl-3-ethyl carbodiimide hydrochloride (51 mg, 0.26 mmol). The reaction was left stirring at room temperature for 18 hours. The reaction was diluted with ethyl acetate, washed with 1N HCl, dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified by reverse phase HPLC (Gilson) to give the title compound. 1H NMR (DMSO, 500 MHz): δ 9.22 (t, J=5.5 Hz, 1H), 7.84 (d, J=8.5 Hz, 2H), 7.79 (d, J=8.9 Hz, 2H), 7.69 (t, J=1.9 Hz, 1H), 7.54 (d, J=1.8 Hz, 2H), 7.17 (d, J=8.2 Hz, 2H), 7.06 (s, 1H), 7.0 (d, J=8.7 Hz, 2H), 5.53 (s, 2H), 4.74 (d, J=5.5 Hz, 2H), 3.79 (s, 3H). LC-MS: 2.32 min; (M+H)=534.3.

Aufarbeitung

  1. waitThe reaction was left
  2. washwashed with 1N HCl
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by reverse phase HPLC (Gilson)

Quellen und Nachweise

ORD-Eintrag
ord-9e720ab79c42417382f57db0e210187c
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US07989475B2

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