Reaktion #731368

ord-07b69f044764476c93665ddb8ea4c80d

Reaktionsgleichung

O=C(O)CC(O)(CC(=O)O)C(=O)O
citric acid
CC(C)(C)OC(=O)NC1CCN(c2ccc(C(=O)Nc3ccccc3C(=O)Nc3ccc(Cl)cn3)c(OC3CCN(C(=O)OC(C)(C)C)CC3)c2)C1
2-[4-[3-(tert-butoxycarbonylamino)pyrrolidin-1-yl]-2-(1-tert-butoxycarbonylpiperidin-4-yloxy)-benzoylamino]-N-(5-chloropyridin-2-yl)benzamide
CC(C)(C)OC(=O)N1CCC(Oc2cc(F)ccc2C(=O)Nc2ccccc2C(=O)Nc2ccc(Cl)cn2)CC1
2-[4-fluoro-2-(1-tert-butoxycarbonylpiperidin-4-yloxy)benzoylamino]-N-(5-chloropyridin-2-yl)benzamide
CC(C)(C)OC(=O)NC1CCNC1
3-tert-butoxycarbonylaminopyrrolidine
→
CC(C)(C)OC(=O)NC1CCN(c2ccc(C(=O)Nc3ccccc3C(=O)Nc3ccc(Cl)cn3)c(OC3CCN(OC(C)(C)C)C(=C=O)C3)c2)C1
2-[4-[3-(tert-Butoxycarbonylamino)pyrrolidin-1-yl]-2-(1-tert-butoxy-carbonylpiperidin-4-yloxy)benzoylamino]-N-(5-chloropyridin-2-yl)benzamide

Edukte

O=C(O)CC(O)(CC(=O)O)C(=O)O
citric acid
CC(C)(C)OC(=O)NC1CCN(c2ccc(C(=O)Nc3ccccc3C(=O)Nc3ccc(Cl)cn3)c(OC3CCN(C(=O)OC(C)(C)C)CC3)c2)C1
2-[4-[3-(tert-butoxycarbonylamino)pyrrolidin-1-yl]-2-(1-tert-butoxycarbonylpiperidin-4-yloxy)-benzoylamino]-N-(5-chloropyridin-2-yl)benzamide
CC(C)(C)OC(=O)N1CCC(Oc2cc(F)ccc2C(=O)Nc2ccccc2C(=O)Nc2ccc(Cl)cn2)CC1
2-[4-fluoro-2-(1-tert-butoxycarbonylpiperidin-4-yloxy)benzoylamino]-N-(5-chloropyridin-2-yl)benzamide
CC(C)(C)OC(=O)NC1CCNC1
3-tert-butoxycarbonylaminopyrrolidine

Reagenzien

Keine

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Vorschrift

Using methods substantially equivalent to those described in Example 4-F except that saturated aqueous citric acid was used instead of water in the workup, 2-[4-[3-(tert-butoxycarbonylamino)pyrrolidin-1-yl]-2-(1-tert-butoxycarbonylpiperidin-4-yloxy)-benzoylamino]-N-(5-chloropyridin-2-yl)benzamide (234 mg, 0.32 mmol, 44%) was prepared from 2-[4-fluoro-2-(1-tert-butoxycarbonylpiperidin-4-yloxy)benzoylamino]-N-(5-chloropyridin-2-yl)benzamide and 3-tert-butoxycarbonylaminopyrrolidine.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07700628B2uspto-grants-2010_04