(Pyrimidin-5-yl)boronic acid → HCID 118195182, compound

HRID 924081Notes

Reaction equation

HRID 924081 reaction equation
Cl[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]([S:16]([C:19]([F:22])([F:21])[F:20])(=[O:18])=[O:17])=[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]([S:16]([C:19]([F:21])([F:20])[F:22])(=[O:18])=[O:17])=[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 89907893HCID 89907893, compound

Product 1

HCID 118195182HCID 118195182, compound

Procedure

The title compound was prepared in an analogous fashion to that described in Example 151 using (R)-5-chloro-6-(3-hydroxypyrrolidin-1-yl)-N-(4-((trifluoromethyl)sulfonyl)phenyl)nicotinamide (Stage 214.1) and pyrimidin-5-ylboronic acid to afford a solid. UPLC-MS (Condition 3), tR=0.92 min, m/z=−492.3; 1H-NMR (400 MHz, DMSO-d6), δ ppm 1.74 (br. s, 1H) 1.85 (br. s, 1H) 2.91 (d, J=10.95 Hz, 1H) 3.18-3.26 (m, 2H) 3.32-3.45 (m, 1H) 4.22 (br. s, 1H) 4.90 (d, J=3.52 Hz, 1H) 8.05-8.16 (m, 3H) 8.16-8.25 (m, 2H) 8.81-8.86 (m, 1H) 8.90 (s, 2H) 9.20 (s, 1H) 10.65 (s, 1H).

Workup

  1. customto afford a solid

Sources & evidence

ORD record
ord-5f743f8b8ba54148bf5eec35860f7c7f
Source dataset
uspto-grants-2016_03
Patent number
US09278981B2

Reaction notes

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