4-Isopropoxybenzeneboronic acid → (S)-8-(2-amino-6-((R)-2,2,2-trifluoro-1-(4'-isopropoxy-3-(piperazin-1-yl)-[1,1'-biphenyl]-4-yl)ethoxy)pyrimidin-4-yl)-2,8-diazaspiro[4.5]decane-3-carboxylic acid

HRID 1499202Notes

Reaction equation

HRID 1499202 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([N:8]2[CH2:32][CH2:31][C:11]3([CH2:15][N:14](C(OCC4C=CC=CC=4)=O)[C@H:13]([C:26]([O:28]CC)=[O:27])[CH2:12]3)[CH2:10][CH2:9]2)[CH:5]=[C:4]([O:33][C@H:34]([C:39]2[CH:44]=[CH:43][C:42](Br)=[CH:41][C:40]=2[N:46]2[CH2:51][CH2:50][N:49](C(OCC3C=CC=CC=3)=O)[CH2:48][CH2:47]2)[C:35]([F:38])([F:37])[F:36])[N:3]=1.[CH:62]([O:65][C:66]1[CH:71]=[CH:70][C:69](B(O)O)=[CH:68][CH:67]=1)([CH3:64])[CH3:63]>>[NH2:1][C:2]1[N:7]=[C:6]([N:8]2[CH2:32][CH2:31][C:11]3([CH2:15][NH:14][C@H:13]([C:26]([OH:28])=[O:27])[CH2:12]3)[CH2:10][CH2:9]2)[CH:5]=[C:4]([O:33][C@H:34]([C:39]2[CH:44]=[CH:43][C:42]([C:69]3[CH:70]=[CH:71][C:66]([O:65][CH:62]([CH3:64])[CH3:63])=[CH:67][CH:68]=3)=[CH:41][C:40]=2[N:46]2[CH2:51][CH2:50][NH:49][CH2:48][CH2:47]2)[C:35]([F:38])([F:36])[F:37])[N:3]=1

Participants

3

Reactant 2

HCID 36987264-Isopropoxybenzeneboronic acidHCID 117952682HCID 117952682, compound

Product 1

HCID 117952495(S)-8-(2-amino-6-((R)-2,2,2-trifluoro-1-(4'-isopropoxy-3-(piperazin-1-yl)-[1,1'-biphenyl]-4-yl)ethoxy)pyrimidin-4-yl)-2,8-diazaspiro[4.5]decane-3-carboxylic acid

Procedure

The title compound was prepared starting with (S)-2-benzyl 3-ethyl 8-(2-amino-6-((R)-1-(2-(4-((benzyloxy)carbonyl)piperazin-1-yl)-4-bromophenyl)-2,2,2-trifluoroethoxy)pyrimidin-4-yl)-2,8-diazaspiro[4.5]decane-2,3-dicarboxylate (intermediate from Step 8, Example 36d] via a Suzuki coupling with (4-isopropoxyphenyl)boronic acid as described for example 54b.

Sources & evidence

ORD record
ord-b7b53ab6977042fa91a08d6b75b5221f
Source dataset
uspto-grants-2015_12
Patent number
US09199994B2

Reaction notes

Loading…