2-Methylpyridine-5-boronic acid → 2-(3-(Hydroxymethyl)azetidin-1-yl)-6'-methyl-N-(4-(trifluoromethoxy)phenyl)-[3,3'-bipyridine]-5-carboxamide

HRID 923972Notes

Reaction equation

HRID 923972 reaction equation
Br[C:2]1[C:3]([N:22]2[CH2:25][CH:24]([CH2:26][OH:27])[CH2:23]2)=[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].[CH3:28][C:29]1[N:34]=[CH:33][C:32](B(O)O)=[CH:31][CH:30]=1>>[OH:27][CH2:26][CH:24]1[CH2:25][N:22]([C:3]2[C:2]([C:32]3[CH:33]=[N:34][C:29]([CH3:28])=[CH:30][CH:31]=3)=[CH:21][C:6]([C:7]([NH:9][C:10]3[CH:15]=[CH:14][C:13]([O:16][C:17]([F:20])([F:19])[F:18])=[CH:12][CH:11]=3)=[O:8])=[CH:5][N:4]=2)[CH2:23]1

Participants

3

Reactant 2

HCID 27630812-Methylpyridine-5-boronic acidHCID 899079805-bromo-6-(3-(hydroxymethyl)azetidin-1-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamide

Product 1

HCID 1181953542-(3-(Hydroxymethyl)azetidin-1-yl)-6'-methyl-N-(4-(trifluoromethoxy)phenyl)-[3,3'-bipyridine]-5-carboxamide

Procedure

The title compound was prepared in an analogous fashion to that described in Example 128 using 5-bromo-6-(3-(hydroxymethyl)azetidin-1-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamide (Stage 135.1) and (6-methylpyridin-3-yl)boronic acid. HPLC (Condition 4) tR=4.18 min, UPLC-MS (Condition 3) tR=0.93 min, m/z=459.2 [M+H]+; 1H-NMR (400 MHz, DMSO-d6) δ ppm 2.48 (s, 3H) 2.58 (t, J=5.87 Hz, 1H) 3.39-3.47 (m, 4H) 3.69 (t, J=8.60 Hz, 2H) 4.66 (t, J=5.28 Hz, 1H) 7.33 (m, J=8.40, 2.50 Hz, 3H) 7.71 (dd, J=7.82, 2.35 Hz, 1H) 7.81-7.86 (m, 2H) 7.95 (d, J=2.35 Hz, 1H) 8.49 (d, J=2.35 Hz, 1H) 8.73 (d, J=1.95 Hz, 1H) 10.17 (s, 1H).

Sources & evidence

ORD record
ord-b70e7351257642ada7e2a61bce44d442
Source dataset
uspto-grants-2016_03
Patent number
US09278981B2

Reaction notes

Loading…