Pyrazole → (R)-6-(3-Hydroxypyrrolidin-1-yl)-5-(1H-pyrazol-5-yl)-N-(4-((trifluoromethyl)thio)phenyl)nicotinamide

HRID 73754Notes

Reaction equation

HRID 73754 reaction equation
Br[C:2]1[C:3]([N:22]2[CH2:26][CH2:25][C@@H:24]([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]([S:16][C:17]([F:20])([F:19])[F:18])=[CH:12][CH:11]=1)=[O:8].[NH:28]1[CH:32]=[CH:31][CH:30]=[N:29]1>>[OH:27][C@@H:24]1[CH2:25][CH2:26][N:22]([C:3]2[C:2]([C:30]3[NH:29][N:28]=[CH:32][CH:31]=3)=[CH:21][C:6]([C:7]([NH:9][C:10]3[CH:15]=[CH:14][C:13]([S: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 1048PyrazoleHCID 86702604(R)-5-bromo-6-(3-hydroxypyrrolidin-1-yl)-N-(4-((trifluoromethyl)thio)phenyl)nicotinamide

Product 1

HCID 72544674(R)-6-(3-Hydroxypyrrolidin-1-yl)-5-(1H-pyrazol-5-yl)-N-(4-((trifluoromethyl)thio)phenyl)nicotinamide

Procedure

The title compound was prepared in an analogous fashion to that described in Example 9 using (R)-5-bromo-6-(3-hydroxypyrrolidin-1-yl)-N-(4-((trifluoromethyl)thio)phenyl)nicotinamide (Stage 11.1) and 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazole to afford a white solid. UPLC-MS (Condition 3) tR=0.97 min, m/z=450.2 [M+H]+, m/z=448.1 [M−H]−; 1H-NMR (400 MHz, DMSO-d6) δ ppm 1.67-1.78 (m, 1H) 1.78-1.88 (m, 1H) 2.94 (d, J=11.92 Hz, 1H) 3.19-3.34 (m, 2H) 3.38-3.50 (m, 1H) 4.20 (br. s, 1H) 4.81-4.93 (m, 1H) 6.33-6.45 (m, 1H) 7.83 (m, J=113.40, 8.20 Hz, 3H) 7.93 (d, J=8.66 Hz, 2H) 7.99-8.08 (m, 1H) 8.70-8.81 (m, 1H) 10.30 (s, 1H) 12.90-13.16 (m, 1H).

Workup

  1. customto afford a white solid

Sources & evidence

ORD record
ord-518282e7c7a24c4ca3fe1c614ab7fbdd
Source dataset
uspto-grants-2014_09
Patent number
US08829195B2

Reaction notes

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