1-(tetrahydro-2H-pyran-2-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole → N-(4-(Chlorodifluoromethoxy)phenyl)-6-(ethyl(2-hydroxyethyl)amino)-5-(1H-pyrazol-5-yl)nicotinamide

HRID 525676Notes

Reaction equation

HRID 525676 reaction equation
Br[C:2]1[C:3]([N:22]([CH2:26][CH3:27])[CH2:23][CH2:24][OH:25])=[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]([Cl:20])([F:19])[F:18])=[CH:12][CH:11]=1)=[O:8].O1CCCCC1[N:34]1[C:38](B2OC(C)(C)C(C)(C)O2)=[CH:37][CH:36]=[N:35]1>>[Cl:20][C:17]([F:19])([F:18])[O:16][C:13]1[CH:14]=[CH:15][C:10]([NH:9][C:7](=[O:8])[C:6]2[CH:21]=[C:2]([C:36]3[NH:35][N:34]=[CH:38][CH:37]=3)[C:3]([N:22]([CH2:26][CH3:27])[CH2:23][CH2:24][OH:25])=[N:4][CH:5]=2)=[CH:11][CH:12]=1

Participants

3

Reactant 2

HCID 115872081-(tetrahydro-2H-pyran-2-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 899068415-bromo-N-(4-(chlorodifluoromethoxy)phenyl)-6-(ethyl(2-hydroxyethyl)amino)nicotinamide

Product 1

HCID 118045135N-(4-(Chlorodifluoromethoxy)phenyl)-6-(ethyl(2-hydroxyethyl)amino)-5-(1H-pyrazol-5-yl)nicotinamide

Procedure

The title compound was prepared in an analogous fashion to that described in Example 26 using 5-bromo-N-(4-(chlorodifluoromethoxy)phenyl)-6-(ethyl(2-hydroxyethyl)amino)nicotinamide (Stage 24.1) and 1-(tetrahydro-2H-pyran-2-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole to afford a yellow solid. UPLC-MS (Condition 3) tR=1.02 min, m/z=452.2 [M+H]+, m/z=450.1 [M−H]−; 1H-NMR (400 MHz, DMSO-d6) δ ppm 0.93 (t, J=7.09 Hz, 3H) 3.17-3.27 (m, 2H) 3.35-3.43 (m, 2H) 3.43-3.53 (m, 2H) 4.59 (br. s, 1H) 6.53 (d, J=1.96 Hz, 1H) 7.33 (d, J=9.05 Hz, 2H) 7.76 (br. s, 1H) 7.82-7.95 (m, 2H) 8.13 (d, J=2.45 Hz, 1H) 8.72 (d, J=2.45 Hz, 1H) 10.29 (s, 1H) 12.98 (br. s, 1H).

Workup

  1. customto afford a yellow solid

Sources & evidence

ORD record
ord-01ae483080024a999a07b16a1e31462f
Source dataset
uspto-grants-2016_05
Patent number
US09340537B2

Reaction notes

Loading…