Reaktion #80164

ord-7441783e4fed4d589eb82a201d1bfcf7

Reaktionsgleichung

COc1ccc(N)c2sc(N)nc12
4-methoxy-benzothiazole-2,7-diamine
CI
iodomethane
O=C(CI)N1CCOCC1
2-iodo-1-morpholin-4-yl-ethanone
O=C([O-])[O-].[K+].[K+]
potassium carbonate
O=C(O)c1ccc(F)cc1
4-fluorobenzoic acid
CN(C)C(On1nnc2cccnc21)=[N+](C)C.F[P-](F)(F)(F)(F)F
HATU
O=C([O-])[O-].[K+].[K+]
potassium carbonate
CCN(C(C)C)C(C)C
N-ethyldiisopropylamine
→
COc1ccc(N(C)CC(=O)N2CCCCC2)c2sc(NC(=O)c3ccc(F)cc3)nc12
4-Fluoro-N-{4-methoxy-7-[methyl-(2-oxo-2-piperidin-1-yl-ethyl)-amino]-benzothiazol-2-yl}-benzamide

Edukte

COc1ccc(N)c2sc(N)nc12
4-methoxy-benzothiazole-2,7-diamine
CI
iodomethane
O=C(CI)N1CCOCC1
2-iodo-1-morpholin-4-yl-ethanone
O=C([O-])[O-].[K+].[K+]
potassium carbonate
O=C(O)c1ccc(F)cc1
4-fluorobenzoic acid
CN(C)C(On1nnc2cccnc21)=[N+](C)C.F[P-](F)(F)(F)(F)F
HATU
O=C([O-])[O-].[K+].[K+]
potassium carbonate
CCN(C(C)C)C(C)C
N-ethyldiisopropylamine

Reagenzien

Keine

Lösungsmittel

C1CCOC1
THF
CN(C)C=O
DMF
CN(C)C=O
DMF

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Vorschrift

From 4-methoxy-benzothiazole-2,7-diamine with potassium carbonate and 2-iodo-1-morpholin-4-yl-ethanone in DMF, then treatment with potassium carbonate and iodomethane in DMF, then treatment with 4-fluorobenzoic acid, HATU and N-ethyldiisopropylamine in THF. ES-MS m/e (%): 457 (M+H+, 100).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06713499B2uspto-grants-2004_03