1-(tetrahydro-2H-pyran-2-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole → (R)-6-(3-Hydroxypyrrolidin-1-yl)-N-(4-(pentafluorosulfanyl)phenyl)-5-(1H-pyrazol-5-yl)nicotinamide

HRID 73770Notes

Reaction equation

HRID 73770 reaction equation
Br[C:2]1[C:3]([N:23]2[CH2:27][CH2:26][C@@H:25]([OH:28])[CH2:24]2)=[N:4][CH:5]=[C:6]([CH:22]=1)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([S:16]([F:21])([F:20])([F:19])([F:18])[F:17])=[CH:12][CH:11]=1)=[O:8].O1CCCCC1[N:35]1[C:39](B2OC(C)(C)C(C)(C)O2)=[CH:38][CH:37]=[N:36]1>>[OH:28][C@@H:25]1[CH2:26][CH2:27][N:23]([C:3]2[C:2]([C:37]3[NH:36][N:35]=[CH:39][CH:38]=3)=[CH:22][C:6]([C:7]([NH:9][C:10]3[CH:11]=[CH:12][C:13]([S:16]([F:20])([F:19])([F:21])([F:17])[F:18])=[CH:14][CH:15]=3)=[O:8])=[CH:5][N:4]=2)[CH2:24]1

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 86702615(R)-5-bromo-6-(3-hydroxypyrrolidin-1-yl)-N-(4-(pentafluorosulfanyl)phenyl)nicotinamide

Product 1

HCID 72544890(R)-6-(3-Hydroxypyrrolidin-1-yl)-N-(4-(pentafluorosulfanyl)phenyl)-5-(1H-pyrazol-5-yl)nicotinamide

Procedure

The title compound was prepared in an analogous fashion to that described in Example 8 using (R)-5-bromo-6-(3-hydroxypyrrolidin-1-yl)-N-(4-(pentafluorosulfanyl)phenyl)nicotinamide (Stage 17.1) and 1-(tetrahydro-2H-pyran-2-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole to afford a beige solid. HPLC (Condition 4) tR=4.68 min, UPLC-MS (Condition 3) tR=0.92 min, m/z=476.3 [M+H]+; 1H-NMR (400 MHz, DMSO-d6) δ ppm 1.64-1.91 (m, 2H) 2.93 (d, J=11.73 Hz, 1H) 3.19-3.34 (m, 2H) 3.36-3.49 (m, 1H) 4.12-4.24 (m, 1H) 4.81 (d, J=3.13 Hz, 1H) 6.38 (s, 1H) 7.73-7.89 (m, 3H) 7.92-8.09 (m, 3H) 8.73 (d, J=1.96 Hz, 1H) 10.37 (s, 1H) 12.82-13.17 (m, 1H).

Workup

  1. customto afford a beige solid

Sources & evidence

ORD record
ord-edd7bef095f641eca6213a1965a00312
Source dataset
uspto-grants-2014_09
Patent number
US08829195B2

Reaction notes

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