Cesium carbonate → 5-[4-(6-Fluoro-benzothiazol-2-yloxy)-benzyl]-hexahydro-pyrrolo[3,4-c]pyrrole-2-carboxylic acid amide

HRID 384529Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 384529
Cl[CH2:2][C:3]1[CH:19]=[CH:18][C:6]([O:7][C:8]2[S:9][C:10]3[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:11]=3[N:12]=2)=[CH:5][CH:4]=1.Cl.[CH2:21]1[CH:25]2[CH2:26][NH:27][CH2:28][CH:24]2[CH2:23][N:22]1[C:29]([NH2:31])=[O:30].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[F:17][C:15]1[CH:14]=[CH:13][C:11]2[N:12]=[C:8]([O:7][C:6]3[CH:18]=[CH:19][C:3]([CH2:2][N:27]4[CH2:26][CH:25]5[CH2:21][N:22]([C:29]([NH2:31])=[O:30])[CH2:23][CH:24]5[CH2:28]4)=[CH:4][CH:5]=3)[S:9][C:10]=2[CH:16]=1

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 57448388Hexahydropyrrolo[3,4-c]pyrrole-2(1h)-carboxamide hydrochlorideHCID 672062122-(4-Chloromethyl-phenoxy)-6-fluoro-benzothiazole

Produkt 1

HCID 425974195-[4-(6-Fluoro-benzothiazol-2-yloxy)-benzyl]-hexahydro-pyrrolo[3,4-c]pyrrole-2-carboxylic acid amideAusbeute 7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a suspension of 2-(4-chloromethyl-phenoxy)-6-fluoro-benzothiazole (152 mg, 0.52 mmol), hexahydro-pyrrolo[3,4-c]pyrrole-2-carboxylic acid amide hydrochloride (110 mg, 0.57 mmol) and Cs2CO3 (676 mg, 2.08 mmol) in DMF (1 mL) was stirred at rt overnight. The resultant mixture was filtered and the residue purified via preparative reverse phase HPLC to afford the title compound (15 mg, 7%). MS (ESI): Mass calcd for C21H21N4O2SF, 412.1; m/z found, 413.1 [M+H]+; 1H NMR (400 MHz, CD3OD): 7.64 (dd, J=8.9, 4.7 Hz, 1H), 7.58 (dd, J=8.4, 2.6 Hz, 1H), 7.47 (d, J=8.5 Hz, 2H), 7.33 (d, J=8.5 Hz, 2H), 7.19 (dt, J=9.0, 8.9, 2.6 Hz, 1H), 3.66 (s, 2H), 3.59-3.40 (m, 2H), 3.29-3.27 (m, 2H), 2.97-2.83 (m, 2H), 2.77 (d, J=9.3, 6.8 Hz, 2H), 2.46 (d, J=9.3, 3.6 Hz, 2H).

Aufarbeitung

  1. filtrationThe resultant mixture was filtered
  2. customthe residue purified via preparative reverse phase HPLC

Quellen und Nachweise

ORD-Eintrag
ord-61a75bde338341fda451355c9f7d635a
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08367719B2

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