Reaction #62523

ord-109f8525376f4356a6f6ffe053381f6f

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
CN(CC1CCCCN1)C1CCCCC1
N-cyclohexyl-N-methyl-piperidin-2-ylmethyl-amine
→
CC(Nc1ncnc2cc(C(=O)N3CCCCC3CN(C)C3CCCCC3)c(Cl)cc12)c1nc2cc(Cl)ccc2[nH]1
6-chloro-4-[(1R/S)-1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-7-{(2R/S)-2-[(N-cyclohexyl-N-methyl-amino)-methyl]-piperidin-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
CN(CC1CCCCN1)C1CCCCC1
N-cyclohexyl-N-methyl-piperidin-2-ylmethyl-amine

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 N-cyclohexyl-N-methyl-piperidin-2-ylmethyl-amine in DMSO at ambient temperature.

Source

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