(Pyrimidin-5-yl)boronic acid → HCID 89907601, compound

HRID 924095Notes

Reaction equation

HRID 924095 reaction equation
Br[C:2]1[C:3]([N:25]2[CH2:29][CH2:28][C@@H:27]([OH:30])[CH2:26]2)=[N:4][CH:5]=[C:6]([CH:24]=1)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17]([F:23])([F:22])[C:18]([F:21])([F:20])[F:19])=[CH:12][CH:11]=1)=[O:8].[N:31]1[CH:36]=[C:35](B(O)O)[CH:34]=[N:33][CH:32]=1>>[OH:30][C@@H:27]1[CH2:28][CH2:29][N:25]([C:3]2[C:2]([C:35]3[CH:36]=[N:31][CH:32]=[N:33][CH:34]=3)=[CH:24][C:6]([C:7]([NH:9][C:10]3[CH:11]=[CH:12][C:13]([O:16][C:17]([F:23])([F:22])[C:18]([F:19])([F:20])[F:21])=[CH:14][CH:15]=3)=[O:8])=[CH:5][N:4]=2)[CH2:26]1

Participants

3

Reactant 2

HCID 2795193(Pyrimidin-5-yl)boronic acidHCID 86702619(R)-5-bromo-6-(3-hydroxypyrrolidin-1-yl)-N-(4-(perfluoroethoxy)phenyl)nicotinamide

Product 1

HCID 89907601HCID 89907601, compound

Procedure

The title compound was prepared in an analogous fashion to that described infashion to that described in Example 185 using (R)-5-bromo-6-(3-hydroxypyrrolidin-1-yl)-N-(4-(perfluoroethoxy)phenyl)nicotinamide (Stage 220.1) and pyrimidin-5-ylboronic acid to afford an off-white solid. HPLC (Condition 4) tR=5.17 min, UPLC-MS (Condition 3) tR=0.99 min, m/z=496.4 [M+H]+; 1H-NMR (400 MHz, DMSO-d6) δ ppm 1.66-1.77 (m, 1H) 1.79-1.91 (m, 1H) 2.88 (d, J=11.34 Hz, 1H) 3.21 (m, J=11.10, 4.90 Hz, 2H) 3.32-3.44 (m, 1H) 4.20 (d, J=2.35 Hz, 1H) 4.87 (d, J=3.52 Hz, 1H) 7.33 (d, J=8.60 Hz, 2H) 7.85 (d, J=9.38 Hz, 2H) 8.08 (d, J=2.35 Hz, 1H) 8.78 (d, J=2.35 Hz, 1H) 8.88 (s, 2H) 9.13-9.34 (m, 1H) 10.16 (s, 1H).

Workup

  1. customto afford an off-white solid

Sources & evidence

ORD record
ord-f35242025252474388767474cf6ad58a
Source dataset
uspto-grants-2016_03
Patent number
US09278981B2

Reaction notes

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