(Pyrimidin-5-yl)boronic acid → HCID 89908206, compound

HRID 923894Notes

Reaction equation

HRID 923894 reaction equation
Br[C:2]1[C:3]([N:22]2[CH2:26][C@@H:25]([O:27][CH3:28])[C@H:24]([OH:29])[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:30]1[CH:35]=[C:34](B(O)O)[CH:33]=[N:32][CH:31]=1>>[OH:29][C@H:24]1[C@H:25]([O:27][CH3:28])[CH2:26][N:22]([C:3]2[C:2]([C:34]3[CH:35]=[N:30][CH:31]=[N:32][CH:33]=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 2795193(Pyrimidin-5-yl)boronic acidHCID 89907977HCID 89907977, compound

Product 1

HCID 89908206HCID 89908206, compound

Procedure

The title compound was prepared in an analogous fashion to that described in Example 54 using 5-bromo-6-(trans-3-hydroxy-4-methoxypyrrolidin-1-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamide (Stage 72.1) and pyrimidin-5-ylboronic acid to afford a white solid. UPLC-MS (condition 1) tR=2.16 min, m/z=476.0 [M+H]+, m/z=474.0 [M−H]−; 1H-NMR (400 MHz, DMSO-d6) δ ppm 2.95 (d, J=11.25 Hz, 1H) 3.14 (d, J=11.98 Hz, 1H) 3.23 (s, 3H) 3.28-3.35 (m, 1H) 3.46 (dd, J=11.98, 4.40 Hz, 1H) 3.61-3.65 (m, 1H) 4.08 (br. s, 1H) 5.19 (d, J=3.67 Hz, 1H) 7.36 (d, J=8.31 Hz, 2H) 7.85 (d, 2H) 8.12 (d, J=2.20 Hz, 1H) 8.79 (d, J=2.45 Hz, 1H) 8.89 (s, 2H) 9.21 (s, 1H) 10.19 (s, 1H).

Workup

  1. customto afford a white solid

Sources & evidence

ORD record
ord-6f64b061ce094b2cbfeee53a7cc0b1be
Source dataset
uspto-grants-2016_03
Patent number
US09278981B2

Reaction notes

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