Reaction #62454

ord-cf7ab2643357470fbd3089a45fcdbfe6

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
CC(C)(C)OC(=O)C(N)C[C@@H]1CCCN1
(2S)-2-(2-tert.-butyloxycarbonyl-aminoethyl)-pyrrolidine
O=C(O)C(F)(F)F
trifluoroacetic acid
→
CC(Nc1ncnc2cc(C(=O)N3CCC[C@H]3CCN)c(Cl)cc12)c1nc2cc(Cl)ccc2[nH]1
7-[(2S)-2-(2-aminoethyl)-pyrrolidin-1-yl-carbonyl]-6-chloro-4-[(1R/S)-1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-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
CC(C)(C)OC(=O)C(N)C[C@@H]1CCCN1
(2S)-2-(2-tert.-butyloxycarbonyl-aminoethyl)-pyrrolidine
O=C(O)C(F)(F)F
trifluoroacetic acid

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 (2S)-2-(2-tert.-butyloxycarbonyl-aminoethyl)-pyrrolidine in DMSO at ambient temperature and subsequent treatment with trifluoroacetic acid.

Source

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