Methyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate → Methyl 4-(4-amino-6-(4-(1-(2-(dimethylamino)ethyl)-4-(4-fluoro-3-(trifluoromethyl)phenyl)-1H-imidazol-2-yl)piperidin-1-yl)pyrimidin-5-yl)benzoate

HRID 2284012Notes

Reaction equation

HRID 2284012 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][CH:35]=2)[CH2:23][CH2:22]1.CC1(C)C(C)(C)OB(C2C=CC([C:54]([O:56][CH3:57])=[O:55])=CC=2)O1>>[NH2:33][C:29]1[C:28]([C:34]2[CH:39]=[CH:38][C:37]([C:54]([O:56][CH3:57])=[O:55])=[CH:36][CH:35]=2)=[C:27]([N:24]2[CH2:23][CH2:22][CH:21]([C:6]3[N:5]([CH2:4][CH2:3][N:2]([CH3:41])[CH3:1])[CH:9]=[C:8]([C:10]4[CH:15]=[CH:14][C:13]([F:16])=[C:12]([C:17]([F:20])([F:19])[F:18])[CH:11]=4)[N:7]=3)[CH2:26][CH2:25]2)[N:32]=[CH:31][N:30]=1

Participants

3

Reactant 2

HCID 2773500Methyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoateHCID 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 89442534Methyl 4-(4-amino-6-(4-(1-(2-(dimethylamino)ethyl)-4-(4-fluoro-3-(trifluoromethyl)phenyl)-1H-imidazol-2-yl)piperidin-1-yl)pyrimidin-5-yl)benzoate

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 methyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate instead of 4-fluorophenyl boronic acid. LC-MS: (M+1=612, obsd.=612).

Sources & evidence

ORD record
ord-b866e570461c4a4f89ab79c86ad0a8d7
Source dataset
uspto-grants-2015_09
Patent number
US09145392B2

Reaction notes

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