3-methyl-1-(oxan-2-yl)-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole → HCID 178422799, compound

HRID 525704Notes

Reaction equation

HRID 525704 reaction equation
Br[C:2]1[C:3]([N:22]2[CH2:25][CH:24]([OH:26])[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].[CH3:27][C:28]1[CH:32]=[C:31](B2OC(C)(C)C(C)(C)O2)[N:30](C2CCCCO2)[N:29]=1>>[OH:26][CH:24]1[CH2:25][N:22]([C:3]2[C:2]([C:31]3[NH:30][N:29]=[C:28]([CH3:27])[CH:32]=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 717576623-methyl-1-(oxan-2-yl)-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 899062825-bromo-6-(3-hydroxyazetidin-1-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamide

Product 1

HCID 178422799HCID 178422799, compound

Procedure

The title compound was prepared in an analogous fashion to that described in Example 37 using 5-bromo-6-(3-hydroxyazetidin-1-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamide (Stage 37.1) and 3-methyl-1-(tetrahydro-2H-pyran-2-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (Stage 41.1) to afford a white lyophilizate. HPLC (Condition 7) tR=5.50 min, UPLC-MS (Condition 3) tR=0.89 min, m/z=434.2 [M+H]+; 1H-NMR (400 MHz, DMSO-d6) δ ppm 2.29 (s, 3H) 3.59-3.67 (m, 2H) 3.99-4.08 (m, 2H) 4.37-4.45 (m, 1H) 6.21 (s, 1H) 7.35 (d, J=8.99 Hz, 2H) 7.82-7.89 (m, J=9.40 Hz, 2H) 8.11 (d, J=1.96 Hz, 1H) 8.66 (d, J=2.35 Hz, 1H) 10.28 (s, 1H).

Workup

  1. customto afford a white lyophilizate

Sources & evidence

ORD record
ord-a2e101005d7b402f965d8b9aa435b2cc
Source dataset
uspto-grants-2016_05
Patent number
US09340537B2

Reaction notes

Loading…