(Pyrimidin-5-yl)boronic acid → (R)-6-(3-Hydroxypyrrolidin-1-yl)-5-(pyrimidin-5-yl)-N-(4-(pentafluorosulfanyl)phenyl)nicotinamide

HRID 924087Notes

Reaction equation

HRID 924087 reaction equation
Br[C:2]1[C:3]([N:23]2[CH2:27][CH2:26][C@@H:25]([OH:28])[CH2:24]2)=[N:4][CH:5]=[C:6]([CH:22]=1)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([S:16]([F:21])([F:20])([F:19])([F:18])[F:17])=[CH:12][CH:11]=1)=[O:8].[N:29]1[CH:34]=[C:33](B(O)O)[CH:32]=[N:31][CH:30]=1>>[OH:28][C@@H:25]1[CH2:26][CH2:27][N:23]([C:3]2[C:2]([C:33]3[CH:34]=[N:29][CH:30]=[N:31][CH:32]=3)=[CH:22][C:6]([C:7]([NH:9][C:10]3[CH:15]=[CH:14][C:13]([S:16]([F:20])([F:19])([F:21])([F:17])[F:18])=[CH:12][CH:11]=3)=[O:8])=[CH:5][N:4]=2)[CH2:24]1

Participants

3

Reactant 2

HCID 2795193(Pyrimidin-5-yl)boronic acidHCID 86702615(R)-5-bromo-6-(3-hydroxypyrrolidin-1-yl)-N-(4-(pentafluorosulfanyl)phenyl)nicotinamide

Product 1

HCID 118195080(R)-6-(3-Hydroxypyrrolidin-1-yl)-5-(pyrimidin-5-yl)-N-(4-(pentafluorosulfanyl)phenyl)nicotinamide

Procedure

The title compound was prepared in an analogous fashion to that described in Example 151 using (R)-5-bromo-6-(3-hydroxypyrrolidin-1-yl)-N-(4-(pentafluorosulfanyl)phenyl)nicotinamide (Stage 216.1) and pyrimidin-5-ylboronic acid to afford a solid. UPLC-MS (Condition 3), tR=0.97 min, m/z=488.2 [M+H]+; 1H-NMR (400 MHz, DMSO-d6), δ ppm 1.74 (m, 1H) 1.84 (m, J=8.99 Hz, 1H) 2.88 (d, J=10.95 Hz, 1H) 3.18-3.26 (m, 2H) 3.33-3.43 (m, 1H) 4.20 (br. s, 1H) 4.83-4.97 (m, 1H) 7.80-7.88 (m, 2H) 7.91-7.99 (m, 2H) 8.10 (d, J=1.00 Hz, 1H) 8.80 (d, J=1.96 Hz, 1H) 8.88 (s, 2H) 9.18 (s, 1H) 10.36 (br. s, 1H).

Workup

  1. customto afford a solid

Sources & evidence

ORD record
ord-509d47ee7b14482c96a7e2b7349f95ee
Source dataset
uspto-grants-2016_03
Patent number
US09278981B2

Reaction notes

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