4-Isopropoxybenzeneboronic acid → (S)-8-(6-((R)-1-([1,1':3',1''-terphenyl]-4'-yl)-2,2,2-trifluoroethoxy)-2-aminopyrimidin-4-yl)-2,8-diazaspiro[4.5]decane-3-carboxylic acid

HRID 1499248Notes

Reaction equation

HRID 1499248 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([N:8]2[CH2:20][CH2:19][C:11]3([CH2:15][NH:14][C@H:13]([C:16]([OH:18])=[O:17])[CH2:12]3)[CH2:10][CH2:9]2)[CH:5]=[C:4]([O:21][C@H:22]([C:27]2[CH:32]=[CH:31][C:30]([C:33]3[CH:38]=[CH:37][C:36](OC(C)C)=[CH:35][CH:34]=3)=[CH:29][C:28]=2[C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[C:23]([F:26])([F:25])[F:24])[N:3]=1.C(OC1C=CC(B(O)O)=CC=1)(C)C>>[C:33]1([C:30]2[CH:31]=[CH:32][C:27]([C@@H:22]([O:21][C:4]3[N:3]=[C:2]([NH2:1])[N:7]=[C:6]([N:8]4[CH2:9][CH2:10][C:11]5([CH2:15][NH:14][C@H:13]([C:16]([OH:18])=[O:17])[CH2:12]5)[CH2:19][CH2:20]4)[CH:5]=3)[C:23]([F:26])([F:24])[F:25])=[C:28]([C:43]3[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=3)[CH:29]=2)[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1

Participants

3

Reactant 2

HCID 36987264-Isopropoxybenzeneboronic acidHCID 117952891(S)-8-(2-amino-6-((R)-2,2,2-trifluoro-1-(4-isopropoxy-[1,1':3',1''-terphenyl]-4'-yl)ethoxy)pyrimidin-4-yl)-2,8-diazaspiro[4.5]decane-3-carboxylic acid

Product 1

HCID 117952311(S)-8-(6-((R)-1-([1,1':3',1''-terphenyl]-4'-yl)-2,2,2-trifluoroethoxy)-2-aminopyrimidin-4-yl)-2,8-diazaspiro[4.5]decane-3-carboxylic acid

Procedure

The title compound was prepared as described above for (S)-8-(2-amino-6-((R)-2,2,2-trifluoro-1-(4-isopropoxy-[1,1′:3′,1″-terphenyl]-4′-yl)ethoxy)pyrimidin-4-yl)-2,8-diazaspiro[4.5]decane-3-carboxylic acid (Example 54b) by substituting phenyl boronic acid for 4-isopropoxyphenyl boronic acid in Step 2.

Sources & evidence

ORD record
ord-d70125dbc4c24c158401245fb4fb1d92
Source dataset
uspto-grants-2015_12
Patent number
US09199994B2

Reaction notes

Loading…