3-methyl-1-(oxan-2-yl)-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole → HCID 178422794, compound

HRID 525770Notes

Reaction equation

HRID 525770 reaction equation
[Cl:1][C:2]([F:27])([F:26])[O:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:25])[C:12]2[CH:17]=[C:16](I)[C:15]([N:19]3[CH2:22][C:21]([OH:24])([CH3:23])[CH2:20]3)=[N:14][CH:13]=2)=[CH:6][CH:5]=1.[CH3:28][C:29]1[CH:33]=[C:32](B2OC(C)(C)C(C)(C)O2)[N:31](C2CCCCO2)[N:30]=1>>[Cl:1][C:2]([F:27])([F:26])[O:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:25])[C:12]2[CH:17]=[C:16]([C:32]3[NH:31][N:30]=[C:29]([CH3:28])[CH:33]=3)[C:15]([N:19]3[CH2:22][C:21]([OH:24])([CH3:23])[CH2:20]3)=[N:14][CH:13]=2)=[CH:6][CH:5]=1

Participants

3

Reactant 2

HCID 717576623-methyl-1-(oxan-2-yl)-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 89906632N-(4-(chlorodifluoromethoxy)phenyl)-6-(3-hydroxy-3-methylazetidin-1-yl)-5-iodonicotinamide

Product 1

HCID 178422794HCID 178422794, compound

Procedure

The title compound was prepared in an analogous fashion to that described in Example 89 using N-(4-(chlorodifluoromethoxy)phenyl)-6-(3-hydroxy-3-methyl azetidin-1-yl)-5-iodonicotinamide (Stage 90.1) and 3-methyl-1-(tetrahydro-2H-pyran-2-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole to give the title product as a white solid. HPLC (Condition 7) tR=5.72 min, UPLC-MS (Condition 8) tR=0.99 min, m/z=464.2 [M+H]+; 1H-NMR (400 MHz, DMSO-d6) δ ppm 1.32 (s, 3H) 2.28 (br. s, 3H) 3.66 (s, 4H) 5.42 (br. s, 1H) 6.16 (s, 1H) 7.33 (d, J=8.60 Hz, 2H) 7.84-7.91 (m, 2H) 8.03 (d, J=2.35 Hz, 1H) 8.71 (s, 1H) 10.21 (s, 1H) 12.63 (br. s, 1H).

Workup

  1. customThe title compound was prepared in an analogous fashion to

Sources & evidence

ORD record
ord-0eaf85ff3a30471bb005a219bfae8158
Source dataset
uspto-grants-2016_05
Patent number
US09340537B2

Reaction notes

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