3-Pyridinylboronic acid → HCID 118195259, compound

HRID 923857Notes

Reaction equation

HRID 923857 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]([O:16][C:17]([F:20])([F:19])[F:18])=[CH:12][CH:11]=1)=[O:8].[N:28]1[CH:33]=[CH:32][CH:31]=[C:30](B(O)O)[CH:29]=1>>[OH:27][C@@H:24]1[CH2:25][CH2:26][N:22]([C:3]2[C:2]([C:30]3[CH:29]=[N:28][CH:33]=[CH:32][CH:31]=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 27343783-Pyridinylboronic acidHCID 86702593(R)-5-bromo-6-(3-hydroxypyrrolidin-1-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamide

Product 1

HCID 118195259HCID 118195259, compound

Procedure

The title compound was prepared in an analogous fashion to that described in Example 36 using (R)-5-bromo-6-(3-hydroxypyrrolidin-1-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamide (Stage 35.1) and pyridin-3-ylboronic acid to afford a yellow solid. UPLC-MS (condition 1) tR=1.82 min, m/z=445.1 [M+H]+, m/z=443.2 [M−H]−; 1H-NMR (400 MHz, DMSO-d6) δ ppm 1.67-1.77 (m, 1H) 1.83 (dd, J=8.80, 4.40 Hz, 1H) 2.87 (d, J=11.49 Hz, 1H) 3.14-3.26 (m, 2H) 3.39-3.45 (m, 1H) 4.18 (d, J=2.45 Hz, 1H) 4.83 (br. s, 1H) 7.34 (d, J=8.31 Hz, 2H) 7.50 (dd, J=7.70, 4.77 Hz, 1H) 7.78-7.90 (m, 3H) 8.03 (d, J=2.20 Hz, 1H) 8.55-8.61 (m, 1H) 8.65 (d, J=1.71 Hz, 1H) 8.77 (d, J=2.45 Hz, 1H) 10.17 (s, 1H).

Workup

  1. customto afford a yellow solid

Sources & evidence

ORD record
ord-47f649c524314769bc1a703e1cf544ca
Source dataset
uspto-grants-2016_03
Patent number
US09278981B2

Reaction notes

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