Reacción #62431

ord-a023bda18d294958af70e82db112169c

Ecuación de reacción

CC(C)(C)OC(=O)n1c(C(CCC(=O)O)Nc2ncnc3cc(C(=O)N4CCCC4)c(Cl)cc23)nc2cc(Cl)ccc21
6-chloro-4-[1-(1-tert.-butyloxycarbonyl-5-chloro-1H-benzimidazol-2-yl)-3-hydroxycarbonyl-propyl-amino]-7-(pyrrolidin-1-yl-carbonyl)-quinazoline
CC(C)(C)OC(=O)NCCN
N-tert.-butyloxycarbonyl-ethylenediamine
CN(C)C(On1nnc2ccccc21)=[N+](C)C.F[B-](F)(F)F
TBTU
O=C(O)C(F)(F)F
trifluoroacetic acid
→
NCCNC(=O)CCC(Nc1ncnc2cc(C(=O)N3CCCC3)c(Cl)cc12)c1nc2cc(Cl)ccc2[nH]1
6-chloro-4-[1-(5-chloro-1H-benzimidazol-2-yl)-3-(aminoethylamino-carbonyl)-propyl-amino]-7-(pyrrolidin-1-yl-carbonyl)-quinazoline

Reactantes

CC(C)(C)OC(=O)n1c(C(CCC(=O)O)Nc2ncnc3cc(C(=O)N4CCCC4)c(Cl)cc23)nc2cc(Cl)ccc21
6-chloro-4-[1-(1-tert.-butyloxycarbonyl-5-chloro-1H-benzimidazol-2-yl)-3-hydroxycarbonyl-propyl-amino]-7-(pyrrolidin-1-yl-carbonyl)-quinazoline
CC(C)(C)OC(=O)NCCN
N-tert.-butyloxycarbonyl-ethylenediamine
CN(C)C(On1nnc2ccccc21)=[N+](C)C.F[B-](F)(F)F
TBTU
O=C(O)C(F)(F)F
trifluoroacetic acid

Reactivos

Ninguno

Disolventes

C1CCOC1.CC#N
acetonitrile tetrahydrofuran

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Procedimiento

Prepared analogously to Example 61 from 6-chloro-4-[1-(1-tert.-butyloxycarbonyl-5-chloro-1H-benzimidazol-2-yl)-3-hydroxycarbonyl-propyl-amino]-7-(pyrrolidin-1-yl-carbonyl)-quinazoline and N-tert.-butyloxycarbonyl-ethylenediamine with TBTU in acetonitrile/tetrahydrofuran and subsequent reaction with trifluoroacetic acid.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US07429597B2uspto-grants-2008_09