1-Ethoxyethene-2-boronic acid pinacol ester → (E)-6-(4-(1-(2-(dimethylamino)ethyl)-4-(4-fluoro-3-(trifluoromethyl)phenyl)-1H-imidazol-2-yl)piperidin-1-yl)-5-(2-ethoxyvinyl)pyrimidin-4-amine

HRID 2284011Notes

Reaction equation

HRID 2284011 reaction equation
[CH3:1][N:2]([CH3:41])[CH2:3][CH2:4][N:5]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[C:12]([C:17]([F:20])([F:19])[F:18])[CH:11]=2)[N:7]=[C:6]1[CH:21]1[CH2:26][CH2:25][N:24]([C:27]2[N:32]=[CH:31][N:30]=[C:29]([NH2:33])[C:28]=2[C:34]2C=CC(F)=C[CH:35]=2)[CH2:23][CH2:22]1.[CH2:42]([O:44]/C=C/B1OC(C)(C)C(C)(C)O1)[CH3:43]>>[CH3:1][N:2]([CH3:41])[CH2:3][CH2:4][N:5]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[C:12]([C:17]([F:19])([F:18])[F:20])[CH:11]=2)[N:7]=[C:6]1[CH:21]1[CH2:22][CH2:23][N:24]([C:27]2[N:32]=[CH:31][N:30]=[C:29]([NH2:33])[C:28]=2/[CH:34]=[CH:35]/[O:44][CH2:42][CH3:43])[CH2:25][CH2:26]1

Participants

3

Reactant 2

HCID 219739081-Ethoxyethene-2-boronic acid pinacol esterHCID 894424846-(4-(1-(2-(dimethylamino)ethyl)-4-(4-fluoro-3-(trifluoromethyl)phenyl)-1H-imidazol-2-yl)piperidin-1-yl)-5-(4-fluorophenyl)pyrimidin-4-amine

Product 1

HCID 89450670(E)-6-(4-(1-(2-(dimethylamino)ethyl)-4-(4-fluoro-3-(trifluoromethyl)phenyl)-1H-imidazol-2-yl)piperidin-1-yl)-5-(2-ethoxyvinyl)pyrimidin-4-amine

Procedure

The title compound was prepared in an analogous manner as 6-(4-(1-(2-(dimethylamino)ethyl)-4-(4-fluoro-3-(trifluoromethyl)phenyl)-1H-imidazol-2-yl)piperidin-1-yl)-5-(4-fluorophenyl)pyrimidin-4-amine using (E)-2-(2-ethoxyvinyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane instead of 4-fluorophenyl boronic acid. LC-MS: (M+1=548, obsd.=548).

Sources & evidence

ORD record
ord-15c654f8f4e14aef85aac5cb5401745f
Source dataset
uspto-grants-2015_09
Patent number
US09145392B2

Reaction notes

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