(Pyrimidin-5-yl)boronic acid → HCID 118195219, compound

HRID 924090Notes

Reaction equation

HRID 924090 reaction equation
Br[C:2]1[C:3]([N:22]2[CH2:26][CH2:25][C@@H:24]([OH: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]([S:16][C:17]([Cl:20])([F:19])[F:18])=[CH:12][CH:11]=1)=[O:8].[N:28]1[CH:33]=[C:32](B(O)O)[CH:31]=[N:30][CH:29]=1>>[Cl:20][C:17]([F:19])([F:18])[S:16][C:13]1[CH:14]=[CH:15][C:10]([NH:9][C:7](=[O:8])[C:6]2[CH:21]=[C:2]([C:32]3[CH:33]=[N:28][CH:29]=[N:30][CH:31]=3)[C:3]([N:22]3[CH2:26][CH2:25][C@@H:24]([OH:27])[CH2:23]3)=[N:4][CH:5]=2)=[CH:11][CH:12]=1

Participants

3

Reactant 2

HCID 2795193(Pyrimidin-5-yl)boronic acidHCID 86702617(R)-5-bromo-N-(4-((chlorodifluoromethyl)thio)phenyl)-6-(3-hydroxypyrrolidin-1-yl)nicotinamide

Product 1

HCID 118195219HCID 118195219, 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-N-(4-((chlorodifluoromethyl)thio)phenyl)-6-(3-hydroxypyrrolidin-1-yl)nicotinamide (Stage 217.1) and pyrimidin-5-ylboronic acid to afford an off-white foam. HPLC (Condition 4) tR=5.27 min, UPLC-MS (Condition 3) tR=1.00 min, m/z=478.3 [M+H]+; 1H-NMR (400 MHz, DMSO-d6) δ ppm 1.66-1.78 (m, 1H) 1.80-1.90 (m, 1H) 2.88 (d, J=11.34 Hz, 1H) 3.21 (m, J=10.90, 4.30 Hz, 2H) 3.32-3.44 (m, 1H) 4.12-4.26 (m, 1H) 4.87 (d, J=3.52 Hz, 1H) 7.67 (d, J=8.60 Hz, 2H) 7.91 (d, J=8.99 Hz, 2H) 8.09 (d, J=2.35 Hz, 1H) 8.79 (d, J=2.35 Hz, 1H) 8.88 (s, 2H) 9.13-9.33 (m, 1H) 10.27 (s, 1H).

Workup

  1. customto afford an off-white foam

Sources & evidence

ORD record
ord-fa42cdf1f2504dea8ee550f10d2d007a
Source dataset
uspto-grants-2016_03
Patent number
US09278981B2

Reaction notes

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