Reaction #62478

ord-fae1f24451cf4bfb816bca0d8eea506f

Reaction equation

CC(Nc1ncnc2cc(C(=O)O)c(Cl)cc12)c1nc2cc(Cl)ccc2[nH]1
6-chloro-4-[1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-7-hydroxycarbonyl-quinazoline
CN(C)C(Oc1c(F)c(F)c(F)c(F)c1F)=[N+](C)C.F[P-](F)(F)(F)(F)F
pentafluorophenyl-tetramethyluronium hexafluorophosphate
CCN(C(C)C)C(C)C
diisopropylethylamine
CC1C=CC(C)N1
2,5-dimethyl-2,5-dihydro-1H-pyrrole
→
CC(Nc1ncnc2cc(C(=O)N3C(C)C=CC3C)c(Cl)cc12)c1nc2cc(Cl)ccc2[nH]1
6-chloro-4-[1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-7-[(2,5-dimethyl-2,5-dihydro-1H-pyrrol-1-yl)-carbonyl]-quinazoline

Reactants

CC(Nc1ncnc2cc(C(=O)O)c(Cl)cc12)c1nc2cc(Cl)ccc2[nH]1
6-chloro-4-[1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-7-hydroxycarbonyl-quinazoline
CN(C)C(Oc1c(F)c(F)c(F)c(F)c1F)=[N+](C)C.F[P-](F)(F)(F)(F)F
pentafluorophenyl-tetramethyluronium hexafluorophosphate
CCN(C(C)C)C(C)C
diisopropylethylamine
CC1C=CC(C)N1
2,5-dimethyl-2,5-dihydro-1H-pyrrole

Reagents

None

Solvents

CS(C)=O
DMSO

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Procedure

Prepared analogously to Example 37a from 6-chloro-4-[1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-7-hydroxycarbonyl-quinazoline, pentafluorophenyl-tetramethyluronium-hexafluorophosphate (PFTU), diisopropylethylamine and 2,5-dimethyl-2,5-dihydro-1H-pyrrole in DMSO at ambient temperature.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07429597B2uspto-grants-2008_09