(Pyrimidin-5-yl)boronic acid → 6-((2-Hydroxyethyl)(methyl)amino)-5-(pyrimidin-5-yl)-N-(4-((trifluoromethyl)thio)phenyl)nicotinamide

HRID 924047Notes

Reaction equation

HRID 924047 reaction equation
Br[C:2]1[C:3]([N:22]([CH2:24][CH2:25][OH:26])[CH3:23])=[N:4][CH:5]=[C:6]([CH:21]=1)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([S:16][C:17]([F:20])([F:19])[F:18])=[CH:12][CH:11]=1)=[O:8].[N:27]1[CH:32]=[C:31](B(O)O)[CH:30]=[N:29][CH:28]=1>>[OH:26][CH2:25][CH2:24][N:22]([CH3:23])[C:3]1[C:2]([C:31]2[CH:32]=[N:27][CH:28]=[N:29][CH:30]=2)=[CH:21][C:6]([C:7]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([S: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 89906571HCID 89906571, compound

Product 1

HCID 899064126-((2-Hydroxyethyl)(methyl)amino)-5-(pyrimidin-5-yl)-N-(4-((trifluoromethyl)thio)phenyl)nicotinamide

Procedure

The title compound was prepared in an analogous fashion to that described in Example 185 using 5-bromo-6-((2-hydroxyethyl)(methyl)amino)-N-(4-((trifluoromethyl)thio)phenyl)nicotinamide (Stage 192.1) and pyrimidin-5-ylboronic acid to afford an off-white solid. HPLC (Condition 4) tR=5.26 min, UPLC-MS (Condition 3) tR=1.00 min, m/z=450.3 [M+H]+; 1H-NMR (400 MHz, DMSO-d6) δ ppm 2.69 (s, 3H) 3.40-3.62 (m, 4H) 4.67 (t, J=1.00 Hz, 1H) 7.69 (d, J=8.60 Hz, 2H) 7.90 (d, J=1.00 Hz, 2H) 8.14 (d, J=2.30 Hz, 1H) 8.76 (d, J=2.50 Hz, 1H) 8.95 (s, 2H) 9.17 (s, 1H) 10.32 (s, 1H).

Workup

  1. customto afford an off-white solid

Sources & evidence

ORD record
ord-9f22ad7f4ae9461d9a997bac3b04b57e
Source dataset
uspto-grants-2016_03
Patent number
US09278981B2

Reaction notes

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