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

HRID 1499247Notes

Reaction equation

HRID 1499247 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]C=3)=[CH:29][C:28]=2C2C=CC=CC=2)[C:23]([F:26])([F:25])[F:24])[N:3]=1.C(O[C:53]1[CH:58]=[CH:57][C:56](B(O)O)=[CH:55][CH:54]=1)(C)C.[CH3:62][C:63]1C=C(B(O)O)C=C[C:68]=1C>>[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]([CH3:35])=[C:63]([CH3:68])[CH:62]=3)=[CH:29][C:28]=2[C:53]2[CH:54]=[CH:55][CH:56]=[CH:57][CH:58]=2)[C:23]([F:25])([F:26])[F:24])[N:3]=1

Participants

4

Reactant 3

HCID 27343483,4-Dimethylphenylboronic acidHCID 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 117952403(S)-8-(2-amino-6-((R)-1-(3,4-dimethyl-[1,1':3',1''-terphenyl]-4'-yl)-2,2,2-trifluoroethoxy)pyrimidin-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 replacing the 4-isopropoxyphenyl boronic acid in Step 2 with 3,4-dimethylphenyl boronic acid.

Sources & evidence

ORD record
ord-e48bc20e554347069449494a1bcab14f
Source dataset
uspto-grants-2015_12
Patent number
US09199994B2

Reaction notes

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