Diisopropylethylamine → HCID 178488474, Verbindung

HRID 1669850Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1669850
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:13]=[C:12]([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=3)[N:11]([CH2:22][C:23]3[CH:31]=[CH:30][C:26]([C:27]([OH:29])=O)=[CH:25][CH:24]=3)[N: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](CC)C(C)C)(C)C.Cl.CN(C)CCCN=C=NCC>C(Cl)Cl.CN(C=O)C.C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:13]=[C:12]([C:14]3[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=3)[N:11]([CH2:22][C:23]3[CH:31]=[CH:30][C:26]([C:27]([NH:38][CH2:37][C:36]4[NH:45][N:33]=[N:34][N:35]=4)=[O:29])=[CH:25][CH:24]=3)[N: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 67335518HCID 67335518, Verbindung

Produkt 1

HCID 178488474HCID 178488474, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 22350042dichloromethane N,N-dimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of the intermediate from example 73 step D (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), N,N-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 DCM, 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 9.21 (t, J=5.3 Hz, 1H), 7.88 (d, J=2.1 Hz, 2H), 7.83 (d, J=8.5 Hz, 2H), 7.56 (t, J=2.1 Hz, 1H), 7.39 (d, J=8.7 Hz, 2H), 7.15 (d, J=8.3 Hz, 2H), 7.12 (s, 1H), 7.04 (d, J=8.7 Hz, 2H), 5.49 (s, 2H), 4.74 (d, J=5.4 Hz, 2H), 3.79 (s, 3H). LC-MS: 3.82 min; (M+H)=534.1.

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-6dbca03a37454ef28fe4d60993c37a10
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US07989475B2

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