Reaktion #638372

ord-84fa544e3da84b6785d6b6c752e8a73d

Reaktionsgleichung

O=C(O)c1ccc(N2CCCCC2=O)c(Cl)c1
3-chloro-4-(piperidin-2-on-1-yl)-benzoic acid
CN(C)C(On1nnc2ccccc21)=[N+](C)C.F[B-](F)(F)F
TBTU
CN1CCOCC1
NMM
COC[C@H](N)c1nc2cc(Cl)ccc2[nH]1
(1R)-1-(5-chloro-1H-benzimidazol-2-yl)-2-methoxyethylamine
→
COC[C@H](NC(=O)c1ccc(N2CCCCC2=O)c(Cl)c1)c1nc2cc(Cl)ccc2[nH]1
3-chloro-N-[(1R)-1-(5-chloro-1H-benzimidazol-2-yl)-2-methoxy-ethyl]-4-(piperidin-2-on-1-yl)-benzamide

Edukte

O=C(O)c1ccc(N2CCCCC2=O)c(Cl)c1
3-chloro-4-(piperidin-2-on-1-yl)-benzoic acid
CN(C)C(On1nnc2ccccc21)=[N+](C)C.F[B-](F)(F)F
TBTU
CN1CCOCC1
NMM
COC[C@H](N)c1nc2cc(Cl)ccc2[nH]1
(1R)-1-(5-chloro-1H-benzimidazol-2-yl)-2-methoxyethylamine

Reagenzien

Keine

Lösungsmittel

CN(C)C=O
DMF

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Vorschrift

Prepared analogously to Example 1f from 3-chloro-4-(piperidin-2-on-1-yl)-benzoic acid, TBTU, NMM and (1R)-1-(5-chloro-1H-benzimidazol-2-yl)-2-methoxyethylamine in DMF and subsequent purification by chromatography on silica gel (eluting gradient: ethyl acetate/ethanol 95:5→90:10).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07947700B2uspto-grants-2011_05