3-methyl-1-(oxan-2-yl)-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole → HCID 178422792, compound

HRID 525761Notes

Reaction equation

HRID 525761 reaction equation
[NH2:1][C@@H:2]1[C@@H:6]([OH:7])[CH2:5][N:4]([C:8]2[CH:27]=[CH:26][C:11]([C:12]([NH:14][C:15]3[CH:20]=[CH:19][C:18]([O:21][C:22]([Cl:25])([F:24])[F:23])=[CH:17][CH:16]=3)=[O:13])=[CH:10][C:9]=2Br)[CH2:3]1.[CH3:29][C:30]1[CH:34]=[C:33](B2OC(C)(C)C(C)(C)O2)[N:32](C2CCCCO2)[N:31]=1>>[NH2:1][C@@H:2]1[C@@H:6]([OH:7])[CH2:5][N:4]([C:8]2[CH:27]=[CH:26][C:11]([C:12]([NH:14][C:15]3[CH:20]=[CH:19][C:18]([O:21][C:22]([Cl:25])([F:24])[F:23])=[CH:17][CH:16]=3)=[O:13])=[CH:10][C:9]=2[C:33]2[NH:32][N:31]=[C:30]([CH3:29])[CH:34]=2)[CH2:3]1

Participants

3

Reactant 2

HCID 717576623-methyl-1-(oxan-2-yl)-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 899064294-((3 S,4S)-3-amino-4-hydroxypyrrolidin-1-yl)-3-bromo-N-(4-(chlorodifluoromethoxy)phenyl)benzamide

Product 1

HCID 178422792HCID 178422792, compound

Procedure

The title compound was prepared in an analogous fashion to that described in Example 76 using 4-((3S,4S)-3-amino-4-hydroxypyrrolidin-1-yl)-3-bromo-N-(4-(chlorodifluoromethoxy)phenyl)benzamide (Stage 76.1) and 3-methyl-1-(tetrahydro-2H-pyran-2-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole to afford the title compound as white solid. HPLC (Condition 7) tR=5.763 min, UPLC-MS (Condition 8) tR=0.82 min, m/z=478.2 [M+H]+; 1H-NMR (400 MHz, DMSO-d6) δ ppm 1.52 (br. s, 2H) 2.26 (br. s, 3H) 2.71-2.86 (m, 2H) 3.10 (br. s, 1H) 3.23-3.38 (m, 2H) 3.67-3.79 (m, 1H) 4.95 (br. s, 1H) 6.09 (s, 1H) 6.77 (d, J=8.21 Hz, 1H) 7.31 (d, J=8.99 Hz, 2H) 7.77-7.94 (m, 4H) 10.08 (s, 1H) 12.45 (br. s, 1H).

Workup

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

Sources & evidence

ORD record
ord-c4a191fb3106441f96f7a6423d3cd3e4
Source dataset
uspto-grants-2016_05
Patent number
US09340537B2

Reaction notes

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