(S)-5-bromo-6-(3-(hydroxymethyl)pyrrolidin-1-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamide → (S)-6-(3-(Hydroxymethyl)pyrrolidin-1-yl)-5-(1H-pyrazol-5-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamide

HRID 73742Notes

Reaction equation

HRID 73742 reaction equation
Br[C:2]1[C:3]([N:22]2[CH2:26][CH2:25][C@H:24]([CH2:27][OH:28])[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]([O:16][C:17]([F:20])([F:19])[F:18])=[CH:12][CH:11]=1)=[O:8].[NH:29]1[CH:33]=[CH:32][C:31](B(O)O)=[N:30]1>>[OH:28][CH2:27][C@H:24]1[CH2:25][CH2:26][N:22]([C:3]2[C:2]([C:31]3[NH:30][N:29]=[CH:33][CH:32]=3)=[CH:21][C:6]([C:7]([NH:9][C:10]3[CH:15]=[CH:14][C:13]([O: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 86702601(S)-5-bromo-6-(3-(hydroxymethyl)pyrrolidin-1-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamideHCID 178514837HCID 178514837, compound

Product 1

HCID 72544671(S)-6-(3-(Hydroxymethyl)pyrrolidin-1-yl)-5-(1H-pyrazol-5-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamide

Procedure

The title compound was prepared in an analogous fashion to that of Example 2 using (S)-5-bromo-6-(3-(hydroxymethyl)pyrrolidin-1-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamide (Stage 7.1) and (1H-pyrazol-3-yl)boronic acid to afford a white solid. UPLC-MS (Condition 1) tR=1.89 min, m/z=448.0 [M+H]+, m/z=446.1 [M−H]−; 1H-NMR (400 MHz, DMSO-d6) δ ppm 1.48-1.64 (m, 1H) 1.77-1.90 (m, 1H) 2.15-2.28 (m, 1H) 3.03 (dd, J=11.25, 6.85 Hz, 1H) 3.22 (br. s, 2H) 3.25-3.31 (m, 2H) 3.34-3.39 (m, 1H) 4.62 (br. s, 1H) 6.39 (br. s, 1H) 7.34 (d, J=8.56 Hz, 2H) 7.51-7.84 (m, 1H) 7.83-7.90 (m, 2H) 8.03 (s, 1H) 8.68-8.79 (m, 1H) 10.19 (s, 1H) 12.87-13.12 (m, 1H).

Workup

  1. customto afford a white solid

Sources & evidence

ORD record
ord-9e0325e4fd7d43cd8fbcaa507644a3c8
Source dataset
uspto-grants-2014_09
Patent number
US08829195B2

Reaction notes

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