2-Aminobenzoxazole → 4-[3-(4-Chloro-phenoxy)-benzyl]-piperazine-1-carboxylic acid benzooxazol-2-ylamide

HRID 331120

Reaktionsgleichung

Reaktionsgleichung von HRID 331120
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH2:10].C1C(=O)N(OC(ON2C(=O)CCC2=O)=O)[C:13](=[O:14])C1.Cl.[Cl:30][C:31]1[CH:50]=[CH:49][C:34]([O:35][C:36]2[CH:37]=[C:38]([CH:46]=[CH:47][CH:48]=2)[CH2:39][N:40]2[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]2)=[CH:33][CH:32]=1.C(N(C(C)C)CC)(C)C>C(Cl)Cl.CCOC(C)=O>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][C:13]([N:43]1[CH2:44][CH2:45][N:40]([CH2:39][C:38]2[CH:46]=[CH:47][CH:48]=[C:36]([O:35][C:34]3[CH:49]=[CH:50][C:31]([Cl:30])=[CH:32][CH:33]=3)[CH:37]=2)[CH2:41][CH2:42]1)=[O:14]

Komponenten

7

Edukt 4

HCID 207072-AminobenzoxazoleHCID 81531DiisopropylethylamineHCID 676246Di(succinimido) carbonateHCID 674138091-[3-(4-Chloro-phenoxy)-benzyl]-piperazine hydrochloride

Produkt 1

HCID 462343144-[3-(4-Chloro-phenoxy)-benzyl]-piperazine-1-carboxylic acid benzooxazol-2-ylamideAusbeute 63,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of benzooxazole-2-ylamine (35.8 mg, 0.267 mmol) in CH2Cl2 (6.0 mL) was added N,N′-disuccinimidyl carbonate (68.4 mg, 0.267 mmol). The reaction mixture was stirred at rt for 6 h, then treated with 1-[3-(4-chloro-phenoxy)-benzyl]-piperazine hydrochloride (100 mg, 0.267 mmol) and diisopropylethylamine (92 μL, 0.536 mmol) and stirred for an additional 16 h at rt. The reaction mixture was diluted with EtOAc (100 mL) and extracted with H2O (100 mL) then saturated aqueous NaCl (50 mL). The organic layer was dried (MgSO4), and concentrated. The crude residue was purified (FCC, 2 N NH3 in MeOH/DCM) to give 4-[3-(4-chloro-phenoxy)-benzyl]-piperazine-1-carboxylic acid benzooxazol-2-ylamide (78.0 mg, 63%). MS (ESI+): calcd for C25H23ClN4O3 m/z 462.15, found 463.5 (M+H)+. 1H NMR (d6-DMSO): 12.13 (br s, 1H), 7.46-7.39 (m, 3H), 7.36 (t, J=7.9, 1H), 7.30 (br s, 1H), 7.22 (t, J=7.6, 1H), 7.18-7.11 (m, 2H), 7.04 (d, J=9.0, 2H), 7.00 (br s, 1H), 6.94-6.91 (m, 1H), 3.73-3.54 (br m, 4H), 3.50 (s, 2H), 2.40-2.31 (m, 4H).

Aufarbeitung

  1. stirringstirred for an additional 16 h at rt
  2. extractionextracted with H2O (100 mL)
  3. dry with materialThe organic layer was dried (MgSO4)
  4. concentrationconcentrated
  5. customThe crude residue was purified (FCC, 2 N NH3 in MeOH/DCM)

Quellen und Nachweise

ORD-Eintrag
ord-6dc392e1500b465c86bbd4470253cb27
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08877769B2

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