(Pyrimidin-5-yl)boronic acid → HCID 89907864, compound

HRID 923943Notes

Reaction equation

HRID 923943 reaction equation
Br[C:2]1[C:3]([N:22]2[CH2:29][CH2:28][C:24]3([CH2:27][O:26][CH2:25]3)[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>>[N:30]1[CH:35]=[C:34]([C:2]2[C:3]([N:22]3[CH2:29][CH2:28][C:24]4([CH2:27][O:26][CH2:25]4)[CH2:23]3)=[N:4][CH:5]=[C:6]([CH:21]=2)[C:7]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][C:17]([F:20])([F:19])[F:18])=[CH:12][CH:11]=2)=[O:8])[CH:33]=[N:32][CH:31]=1

Participants

3

Reactant 2

HCID 2795193(Pyrimidin-5-yl)boronic acidHCID 118195257HCID 118195257, compound

Product 1

HCID 89907864HCID 89907864, compound

Procedure

The title compound was prepared in an analogous fashion to that described in Example 86 using 5-bromo-6-(2-oxa-6-azaspiro[3.4]octan-6-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamide (Stage 116.1) and pyrimidin-5-ylboronic acid to afford a white solid. UPLC-MS (condition 1) tR=2.35 min, m/z=472.0 [M+H]+, m/z=470.0 [M−H]−; 1H-NMR (400 MHz, DMSO-d6) δ ppm 2.00-2.15 (m, 2H) 3.11 (t, J=6.72 Hz, 2H) 3.44 (s, 2H) 4.41-4.45 (m, 2H) 4.45-4.50 (m, 2H) 7.36 (d, J=8.31 Hz, 2H) 7.85 (d, J=9.05 Hz, 2H) 8.11 (d, J=2.45 Hz, 1H) 8.79 (d, J=2.45 Hz, 1H) 8.90 (s, 2H) 9.20 (s, 1H) 10.19 (s, 1H).

Workup

  1. customto afford a white solid

Sources & evidence

ORD record
ord-09d3adfd800d4f40a1e090a55e8fa192
Source dataset
uspto-grants-2016_03
Patent number
US09278981B2

Reaction notes

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