2-Ethenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane → 6-{4-[1-(2-Dimethylamino-ethyl)-4-(4-fluoro-3-trifluoromethyl-phenyl)-1H-imidazol-2-yl]-piperidin-1-yl}-5-vinyl-pyrimidin-4-ylamine

HRID 2283998Notes

Reaction equation

HRID 2283998 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.C(B1OC(C)(C)C(C)(C)O1)=C>>[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:18])[F:19])[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]=[CH2:35])[CH2:25][CH2:26]1

Participants

3

Reactant 2

HCID 52330122-Ethenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 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 894426406-{4-[1-(2-Dimethylamino-ethyl)-4-(4-fluoro-3-trifluoromethyl-phenyl)-1H-imidazol-2-yl]-piperidin-1-yl}-5-vinyl-pyrimidin-4-ylamine

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-fluoro-phenyl)-pyrimidin-4-ylamine using vinylboronic acid pinacol ester instead of 4-fluorophenylboronic acid. LC-MS: (M+1=504, obsd.=504).

Sources & evidence

ORD record
ord-a59086c0da0542338b79399ab4d54f1a
Source dataset
uspto-grants-2015_09
Patent number
US09145392B2

Reaction notes

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