1-(tetrahydro-2H-pyran-2-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole → HCID 72544446, compound

HRID 73799Notes

Reaction equation

HRID 73799 reaction equation
Br[C:2]1[C:3]([N:24]2[CH2:28][CH2:27][C@@H:26]([OH:29])[CH2:25]2)=[N:4][CH:5]=[C:6]([CH:23]=1)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([F:22])([F:21])[C:17]([Cl:20])([F:19])[F:18])=[CH:12][CH:11]=1)=[O:8].O1CCCCC1[N:36]1[C:40](B2OC(C)(C)C(C)(C)O2)=[CH:39][CH:38]=[N:37]1>>[Cl:20][C:17]([F:19])([F:18])[C:16]([C:13]1[CH:14]=[CH:15][C:10]([NH:9][C:7](=[O:8])[C:6]2[CH:23]=[C:2]([C:38]3[NH:37][N:36]=[CH:40][CH:39]=3)[C:3]([N:24]3[CH2:28][CH2:27][C@@H:26]([OH:29])[CH2:25]3)=[N:4][CH:5]=2)=[CH:11][CH:12]=1)([F:22])[F:21]

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 86702630(R)-5-bromo-N-(4-(2-chloro-1,1,2,2-tetrafluoroethyl)phenyl)-6-(3-hydroxypyrrolidin-1-yl)nicotinamide

Product 1

HCID 72544446HCID 72544446, compound

Procedure

The title compound was prepared in an analogous fashion to that described in Example 8 using (R)-5-bromo-N-(4-(2-chloro-1,1,2,2-tetrafluoroethyl)phenyl)-6-(3-hydroxypyrrolidin-1-yl)nicotinamide (Stage 31.1) and 1-(tetrahydro-2H-pyran-2-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole to afford a white powder. HPLC (Condition 4) tR=4.89 min, UPLC-MS (Condition 3) tR=0.98 min, m/z=484.1 [M+H]+; 1H-NMR (400 MHz, DMSO-d6) δ ppm 1.65-1.89 (m, 2H) 2.83-2.98 (m, 1H) 3.18-3.33 (m, 2H) 3.36-3.49 (m, 1H) 4.13-4.24 (m, 1H) 4.77-4.93 (m, 1H) 6.31-6.43 (m, 1H) 7.62 (d, J=8.59 Hz, 2H) 7.77-7.84 (m, 1H) 7.91-8.09 (m, 3H) 8.64-8.81 (m, 1H) 10.31 (s, 1H) 12.83-12.96 (m, 1H).

Workup

  1. customto afford a white powder

Sources & evidence

ORD record
ord-c468623c28fa4a0993f1606fb46d03ff
Source dataset
uspto-grants-2014_09
Patent number
US08829195B2

Reaction notes

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