(Pyrimidin-5-yl)boronic acid → HCID 118195190, compound

HRID 924072Notes

Reaction equation

HRID 924072 reaction equation
Br[C:2]1[C:3]([N:24]2[CH2:28][CH2:27][C@@H:26]([OH:29])[CH2:25]2)=[N:4][CH:5]=[C:6]([CH:23]=1)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([F:22])([F:21])[C:17]([F:20])([F:19])[F:18])=[CH:12][CH:11]=1)=[O:8].[N:30]1[CH:35]=[C:34](B(O)O)[CH:33]=[N:32][CH:31]=1>>[OH:29][C@@H:26]1[CH2:27][CH2:28][N:24]([C:3]2[C:2]([C:34]3[CH:35]=[N:30][CH:31]=[N:32][CH:33]=3)=[CH:23][C:6]([C:7]([NH:9][C:10]3[CH:11]=[CH:12][C:13]([C:16]([F:21])([F:22])[C:17]([F:18])([F:19])[F:20])=[CH:14][CH:15]=3)=[O:8])=[CH:5][N:4]=2)[CH2:25]1

Participants

3

Reactant 2

HCID 2795193(Pyrimidin-5-yl)boronic acidHCID 86702613HCID 86702613, compound

Product 1

HCID 118195190HCID 118195190, compound

Procedure

The title compound was prepared in an analogous fashion to that described in Example 185 using (R)-5-bromo-6-(3-hydroxypyrrolidin-1-yl)-N-(4-(perfluoroethyl)phenyl)nicotinamide (Stage 208.1) and pyrimidin-5-ylboronic acid to afford a foam. HPLC (Condition 4) tR=5.11 min, UPLC-MS (Condition 3) tR=1.00 min, m/z=480.2 [M+H]+; 1H-NMR (400 MHz, DMSO-d6) δ ppm 1.68-1.79 (m, 1H) 1.85 (m, J=9.00 Hz, 1H) 2.88 (d, J=11.73 Hz, 1H) 3.14-3.27 (m, 2H) 3.38 (m, J=7.00 Hz, 1H) 4.20 (m, J=2.30 Hz, 1H) 4.87 (d, J=3.52 Hz, 1H) 7.66 (d, J=8.60 Hz, 2H) 7.99 (d, J=8.60 Hz, 2H) 8.10 (d, J=2.35 Hz, 1H) 8.80 (d, J=1.96 Hz, 1H) 8.88 (s, 2H) 9.18 (s, 1H) 10.31 (s, 1H).

Workup

  1. customto afford a foam

Sources & evidence

ORD record
ord-705019717f7942ad8fda89f4fb3dc46c
Source dataset
uspto-grants-2016_03
Patent number
US09278981B2

Reaction notes

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