(Pyrimidin-5-yl)boronic acid → 6-Methyl-5-(pyrimidin-5-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamide

HRID 629077Notes

Reaction equation

HRID 629077 reaction equation
Cl[C:2]1[C:3]([CH3:22])=[N:4][CH:5]=[C:6]([CH:21]=1)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17]([F:20])([F:19])[F:18])=[CH:12][CH:11]=1)=[O:8].[N:23]1[CH:28]=[C:27](B(O)O)[CH:26]=[N:25][CH:24]=1>>[CH3:22][C:3]1[C:2]([C:27]2[CH:28]=[N:23][CH:24]=[N:25][CH:26]=2)=[CH:21][C:6]([C:7]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][C:17]([F:20])([F:19])[F:18])=[CH:12][CH:11]=2)=[O:8])=[CH:5][N:4]=1

Participants

3

Reactant 2

HCID 2795193(Pyrimidin-5-yl)boronic acidHCID 899068685-chloro-6-methyl-N-(4-(trifluoromethoxy)phenyl)nicotinamide

Product 1

HCID 722034196-Methyl-5-(pyrimidin-5-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamide

Procedure

The title compound was prepared in an analogous fashion to that described in Example 40 using 5-chloro-6-methyl-N-(4-(trifluoromethoxy)phenyl)nicotinamide (Stage 43.1) and pyrimidin-5-ylboronic acid. UPLC-MS (Condition 1) tR=2.10 min, m/z=375.0 [M+H]+, m/z=373.0 [M−H]−; 1H-NMR (400 MHz, DMSO-d6) δ ppm 2.57 (s, 3H) 7.40 (d, J=8.80 Hz, 2H) 7.88 (d, J=9.29 Hz, 2H) 8.30 (d, J=2.20 Hz, 1H) 9.03 (s, 2H) 9.08 (d, J=2.20 Hz, 1H) 9.29 (s, 1H) 10.55 (s, 1H).

Sources & evidence

ORD record
ord-0334d5e2242d4f2f910f7df4229d8731
Source dataset
uspto-grants-2016_04
Patent number
US09315489B2

Reaction notes

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