1-(2-Bromophenyl)-2,2,2-trifluoroethanone → (S)-8-(6-((R)-1-([1,1'-biphenyl]-2-yl)-2,2,2-trifluoroethoxy)-2-amino pyrimidin-4-yl)-2,8-diazaspiro[4.5]decane-3-carboxylic acid

HRID 1499204Notes

Reaction equation

HRID 1499204 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](Cl)=[CH:29][C:28]=2[C:34]2[CH:39]=[CH:38][CH:37]=[C:36](S(=O)(=O)N)[CH:35]=2)[C:23]([F:26])([F:25])[F:24])[N:3]=1.BrC1C=CC=CC=1C(=O)C(F)(F)F>>[C:28]1([C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=1[C@@H:22]([O:21][C:4]1[N:3]=[C:2]([NH2:1])[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]=1)[C:23]([F:24])([F:25])[F:26]

Participants

3

Reactant 2

HCID 3586161-(2-Bromophenyl)-2,2,2-trifluoroethanoneHCID 117952268(3S)-8-[2-amino-6-[(1R)-1-[4-chloro-2-(3-sulfamoylphenyl)phenyl]-2,2,2-trifluoroethoxy]pyrimidin-4-yl]-2,8-diazaspiro[4.5]decane-3-carboxylic acid

Product 1

HCID 117953011(S)-8-(6-((R)-1-([1,1'-biphenyl]-2-yl)-2,2,2-trifluoroethoxy)-2-amino pyrimidin-4-yl)-2,8-diazaspiro[4.5]decane-3-carboxylic acid

Procedure

The title compound was prepared as described for (S)-8-(2-amino-6-((R)-1-(5-chloro-3′-sulfamoyl-[1,1′-biphenyl]-2-yl)-2,2,2-trifluoroethoxy)pyrimidin-4-yl)-2,8-diazaspiro[4.5]decane-3-carboxylic acid (Example 34u) starting with 1-(2-bromophenyl)-2,2,2-trifluoroethanone.

Sources & evidence

ORD record
ord-3273fdb6f2b1467e8bf8893b9726d0c7
Source dataset
uspto-grants-2015_12
Patent number
US09199994B2

Reaction notes

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