3-methyl-1-(oxan-2-yl)-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole → HCID 178422798, compound

HRID 525707Notes

Reaction equation

HRID 525707 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[CH:33]=[C:32](B2OC(C)(C)C(C)(C)O2)[N:31](C2CCCCO2)[N:30]=1>>[OH:27][CH2:26][CH:24]1[CH2:25][N:22]([C:3]2[C:2]([C:32]3[NH:31][N:30]=[C:29]([CH3:28])[CH:33]=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 899079805-bromo-6-(3-(hydroxymethyl)azetidin-1-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamide

Product 1

HCID 178422798HCID 178422798, compound

Procedure

The title compound was prepared in an analogous fashion to that described in Example 41 using 5-bromo-6-(3-(hydroxymethyl)azetidin-1-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamide (Stage 39.1) 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 beige lyophilizate. HPLC (Condition 7) tR=5.488 min, UPLC-MS (Condition 3) tR=0.89 min, m/z=448.1 [M+H]+; 1H-NMR (400 MHz, DMSO-d6) δ ppm 2.27 (s, 3H) 2.56-2.69 (m, 1H) 3.46 (d, J=6.26 Hz, 2H) 3.51-3.57 (m, 2H) 3.79 (t, J=8.6 Hz, 2H) 6.16 (s, 1H) 7.34 (d, J=8.60 Hz, 2H) 7.83-7.90 (m, J=9.00 Hz, 2H) 8.01 (d, J=2.35 Hz, 1H) 8.70 (d, J=2.35 Hz, 1H) 10.20 (br.s, 1H), 12.04 (br.s, 1H).

Workup

  1. customto afford a beige lyophilizate

Sources & evidence

ORD record
ord-b561ffdb289a4a71808de5d547b24c11
Source dataset
uspto-grants-2016_05
Patent number
US09340537B2

Reaction notes

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