HCID 89906910, compound → HCID 89908440, compound

HRID 525658Notes

Reaction equation

HRID 525658 reaction equation
Br[C:2]1[C:3]([N:22]2[CH2:26][CH2:25][C@:24]([OH:28])([CH3:27])[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].[NH:29]1[CH:33]=[CH:32][C:31](B(O)O)=[N:30]1>CCCCCCC.CCO.CO>[OH:28][C@:24]1([CH3:27])[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

4

Reactant 2

HCID 89906910HCID 89906910, compoundHCID 178514837HCID 178514837, compound

Product 1

HCID 89908440HCID 89908440, compound

Reagents, catalysts & solvents 1

HCID 22386818heptane EtOH MeOHSolvent

Procedure

The title compound was prepared in an analogous fashion to that described in Example 15 using (R)-5-bromo-6-(3-hydroxy-3-methylpyrrolidin-1-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamide (Stage 14.1) and (1H-pyrazol-3-yl)boronic acid to afford a white solid. HPLC Chiral (CHIRALCEL® OD-H, 250×4.6 mm, eluent: n-heptane/EtOH/MeOH (80:12:8), 1 mL/min, UV 210 nm) tR=5.49 min, UPLC-MS (Condition 3) tR=0.93 min, m/z=448.3 [M+H]+, m/z=446.1 [M−H]−, 492.1 [M+formic acid-H]−; 1H-NMR (400 MHz, DMSO-d6) δ ppm 1.20 (s, 3H) 1.65-1.81 (m, 2H) 2.99 (d, J=10.54 Hz, 1H) 3.06 (d, J=11.80 Hz, 1H) 3.24-3.33 (m, 1H) 3.48 (td, J=10.20, 7.22 Hz, 1H) 4.68 (s, 1H) 6.38 (d, J=2.01 Hz, 1H) 7.33 (d, J=9.16 Hz, 2H) 7.75 (br. s, 1H) 7.83-7.90 (m, 2H) 8.03 (d, J=2.51 Hz, 1H) 8.73 (d, J=2.38 Hz, 1H) 10.19 (br. s, 1H) 12.96 (br. s, 1H).

Workup

  1. customto afford a white solid

Sources & evidence

ORD record
ord-ab04404f59c041518fd2901ed227780c
Source dataset
uspto-grants-2016_05
Patent number
US09340537B2

Reaction notes

Loading…