Reaktion #62433

ord-d04d007c7be8465d84b937f9247f909e

Reaktionsgleichung

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
NC1CCN(c2ncncn2)CC1
1-[1,3,5]triazin-2-yl-piperidin-4-ylamine
CN(C)C(On1nnc2ccccc21)=[N+](C)C.F[B-](F)(F)F
TBTU
O=C(O)C(F)(F)F
trifluoroacetic acid
→
O=C(CCC(Nc1ncnc2cc(C(=O)N3CCCC3)c(Cl)cc12)c1nc2cc(Cl)ccc2[nH]1)NC1CCN(c2ncncn2)CC1
6-chloro-4-{1-(5-chloro-1H-benzimidazol-2-yl)-3-[(1-[1,3,5]triazin-2-yl-piperidin-4-ylamino)-carbonyl]-propyl-amino}-7-(pyrrolidin-1-yl-carbonyl)-quinazoline

Edukte

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
NC1CCN(c2ncncn2)CC1
1-[1,3,5]triazin-2-yl-piperidin-4-ylamine
CN(C)C(On1nnc2ccccc21)=[N+](C)C.F[B-](F)(F)F
TBTU
O=C(O)C(F)(F)F
trifluoroacetic acid

Reagenzien

Keine

Lösungsmittel

C1CCOC1.CC#N
acetonitrile tetrahydrofuran

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Vorschrift

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 1-[1,3,5]triazin-2-yl-piperidin-4-ylamine with TBTU in acetonitrile/tetrahydrofuran and subsequent reaction with trifluoroacetic acid.

Quelle

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