(S)-1-(2-methoxy-1-phenylethyl)urea → trans-2-(6-(3-((S)-2-methoxy-1-phenylethyl)ureido)-1-trityl-1H-pyrazolo[4,3-c]pyridin-3-yl)cyclopropanecarboxylic acid

HRID 571414Notes

Reaction equation

HRID 571414 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]2[C:8]([C@@H:30]3[CH2:32][C@H:31]3[C:33]([O:35]CC)=[O:34])=[N:9][N:10]([C:11]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:4]=2[CH:3]=1.[CH3:38][O:39][CH2:40][C@@H:41]([NH:48][C:49]([NH2:51])=[O:50])[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1>>[CH3:38][O:39][CH2:40][C@@H:41]([NH:48][C:49](=[O:50])[NH:51][C:2]1[N:7]=[CH:6][C:5]2[C:8]([C@@H:30]3[CH2:32][C@H:31]3[C:33]([OH:35])=[O:34])=[N:9][N:10]([C:11]([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:4]=2[CH:3]=1)[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1

Participants

3

Reactant 2

HCID 89524417(S)-1-(2-methoxy-1-phenylethyl)ureaHCID 131732820trans-ethyl 2-(6-chloro-1-trityl-1H-pyrazolo[4,3-c]pyridin-3-yl)cyclopropanecarboxylate

Product 1

HCID 89525877trans-2-(6-(3-((S)-2-methoxy-1-phenylethyl)ureido)-1-trityl-1H-pyrazolo[4,3-c]pyridin-3-yl)cyclopropanecarboxylic acid

Procedure

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.

Sources & evidence

ORD record
ord-1cd38a321fea45379fe959d663b0be0d
Source dataset
uspto-grants-2015_05
Patent number
US09023865B2

Reaction notes

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