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

HRID 2284010Notes

Reaction equation

HRID 2284010 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]2[CH:39]=[CH:38][C:37](F)=[CH:36]C=2)[CH2:23][CH2:22]1.C1(/C=C/B2OC(C)(C)C(C)(C)O2)CC1>>[CH:38]1(/[CH:39]=[CH:34]/[C:28]2[C:29]([NH2:33])=[N:30][CH:31]=[N:32][C:27]=2[N:24]2[CH2:23][CH2:22][CH:21]([C:6]3[N:5]([CH2:4][CH2:3][N:2]([CH3:1])[CH3:41])[CH:9]=[C:8]([C:10]4[CH:15]=[CH:14][C:13]([F:16])=[C:12]([C:17]([F:19])([F:18])[F:20])[CH:11]=4)[N:7]=3)[CH2:26][CH2:25]2)[CH2:37][CH2:36]1

Participants

3

Reactant 2

HCID 16217940(E)-2-Cyclopropylethylene-1-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 89450671(E)-5-(2-cyclopropylvinyl)-6-(4-(1-(2-(dimethylamino)ethyl)-4-(4-fluoro-3-(trifluoromethyl)phenyl)-1H-imidazol-2-yl)piperidin-1-yl)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-cyclopropylvinyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane instead of 4-fluorophenyl boronic acid. LC-MS: (M+1=544, obsd.=544).

Sources & evidence

ORD record
ord-d30c5dbf630442b6ad74cc762b09f9f0
Source dataset
uspto-grants-2015_09
Patent number
US09145392B2

Reaction notes

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