Trifluoroacetic acid → 2-Amino-1-{5-[4-(benzothiazol-2-yloxy)-benzyl]-hexahydro-pyrrolo[3,4-b]pyrrol-1-yl}-ethanone

HRID 1799078Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1799078
Cl.[NH:2]1[CH2:6][CH2:5][CH:4]2[CH2:7][N:8]([CH2:10][C:11]3[CH:26]=[CH:25][C:14]([O:15][C:16]4[S:17][C:18]5[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=5[N:20]=4)=[CH:13][CH:12]=3)[CH2:9][CH:3]12.CCN(CC)CC.C([NH:41][CH2:42][C:43](O)=[O:44])(OC(C)(C)C)=O.Cl.CN(C)CCCN=C=NCC.FC(F)(F)C(O)=O>C(Cl)Cl.CO.CS(C)=O>[NH2:41][CH2:42][C:43]([N:2]1[CH2:6][CH2:5][CH:4]2[CH2:7][N:8]([CH2:10][C:11]3[CH:26]=[CH:25][C:14]([O:15][C:16]4[S:17][C:18]5[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=5[N:20]=4)=[CH:13][CH:12]=3)[CH2:9][CH:3]12)=[O:44]

Komponenten

8

Edukt 5

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 78288N-(tert-butoxycarbonyl)glycineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 425990812-[4-(Hexahydro-pyrrolo[3,4-b]pyrrol-5-ylmethyl)-phenoxy]-benzothiazole hydrochloride

Produkt 1

HCID 425995902-Amino-1-{5-[4-(benzothiazol-2-yloxy)-benzyl]-hexahydro-pyrrolo[3,4-b]pyrrol-1-yl}-ethanoneAusbeute 35 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 22036561Dimethyl sulfoxide methanolLösungsmittel

Versuchsvorschrift

To a stirred solution of 2-[4-(hexahydro-pyrrolo[3,4-b]pyrrol-5-ylmethyl)-phenoxy]-benzothiazole hydrochloride (100 mg, 0.26 mmol) and Et3N (215 μL, 1.6 mmol) in CH2Cl2 (2 mL) was added N-Boc-glycine (95 mg, 0.5 mmol), and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (104 mg, 0.5 mmol). The resulting solution was then stirred at rt for 16 h. The resulting mixture was then treated with trifluoroacetic acid (1 mL) at rt for 3 h. The crude solid was dissolved in CH3OH/DMSO (2:1) and purified via reverse phase preparative HPLC to yield the title compound as a fluffy white solid (37 mg, 35%). MS (ESI): mass calcd. for C22H24N4O2S, 408.5; m/z found, 409.2 [M+H]+. 1H NMR (500 MHz, CDCl3): 7.74 (d, J=8.1 Hz, 1H), 7.68 (d, J=8.0 Hz, 1H), 7.43-7.33 (m, 3H), 7.33-7.26 (m, 3H), 4.51-4.42 (m, 1H), 4.27-4.19 (m, 0.5H), 4.02-3.92 (m, 0.5H), 3.66 (d, J=13.2 Hz, 1H), 3.58 (d, J=5.0 Hz, 0.5H), 3.51-3.37 (m, 3H), 3.28 (d, J=16.7 Hz, 0.5H), 2.91-2.76 (m, 2H), 2.70-2.60 (m, 1H), 2.58-2.50 (m, 1H), 2.50-2.37 (m, 1H), 2.14-1.96 (m, 1H), 1.97-1.80 (m, 1H).

Aufarbeitung

  1. custompurified via reverse phase preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-f0ed4ea37145451f871cf36fa6e92b16
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08344008B2

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