Reaktion #658596

ord-1cd38a321fea45379fe959d663b0be0d

Reaktionsgleichung

CCOC(=O)[C@@H]1C[C@H]1c1nn(C(c2ccccc2)(c2ccccc2)c2ccccc2)c2cc(Cl)ncc12
trans-ethyl 2-(6-chloro-1-trityl-1H-pyrazolo[4,3-c]pyridin-3-yl)cyclopropanecarboxylate
COC[C@@H](NC(N)=O)c1ccccc1
(S)-1-(2-methoxy-1-phenylethyl)urea
→
COC[C@@H](NC(=O)Nc1cc2c(cn1)c([C@@H]1C[C@H]1C(=O)O)nn2C(c1ccccc1)(c1ccccc1)c1ccccc1)c1ccccc1
trans-2-(6-(3-((S)-2-methoxy-1-phenylethyl)ureido)-1-trityl-1H-pyrazolo[4,3-c]pyridin-3-yl)cyclopropanecarboxylic acid

Edukte

CCOC(=O)[C@@H]1C[C@H]1c1nn(C(c2ccccc2)(c2ccccc2)c2ccccc2)c2cc(Cl)ncc12
trans-ethyl 2-(6-chloro-1-trityl-1H-pyrazolo[4,3-c]pyridin-3-yl)cyclopropanecarboxylate
COC[C@@H](NC(N)=O)c1ccccc1
(S)-1-(2-methoxy-1-phenylethyl)urea

Reagenzien

Keine

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Vorschrift

In a manner similar to that described in Example 30 (Step 1), trans-ethyl 2-(6-chloro-1-trityl-1H-pyrazolo[4,3-c]pyridin-3-yl)cyclopropanecarboxylate was reacted with (S)-1-(2-methoxy-1-phenylethyl)urea (BrettPhos precatalyst, KOtBu, dioxane, 80° C.) to provide trans-2-(6-(3-((S)-2-methoxy-1-phenylethyl)ureido)-1-trityl-1H-pyrazolo[4,3-c]pyridin-3-yl)cyclopropanecarboxylic acid. MS ESI calc'd. for C39H35N5O4[M+1]+ 638, found 638.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US09023865B2uspto-grants-2015_05