(Pyrimidin-5-yl)boronic acid → HCID 67497531, compound

HRID 1628349Notes

Reaction equation

HRID 1628349 reaction equation
Br[C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:25])[C@@H:10]([NH:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:5]=[CH:6][CH:7]=1.[N:26]1[CH:31]=[C:30](B(O)O)[CH:29]=[N:28][CH:27]=1>>[O:25]=[C:9]([NH:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([C:30]2[CH:31]=[N:26][CH:27]=[N:28][CH:29]=2)[CH:3]=1)[C@@H:10]([NH:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

3

Reactant 2

HCID 2795193(Pyrimidin-5-yl)boronic acidHCID 67498417HCID 67498417, compound

Product 1

HCID 67497531HCID 67497531, compoundYield 41%

Procedure

The title compound was prepared from 107.1.B and pyrimidin-5-ylboronic acid according to the procedure described in Example 107.1.C. The crude product was purified to give 108.1.A (85 mg, 41% yield) as colorless crystals. 1H NMR (400 MHz, CDCl3) δ ppm 9.59 (s, 1H), 9.23 (s, 1H), 8.99 (s, 2H), 7.98 (t, J=1.9 Hz, 1H), 7.66-7.62 (m, 1H), 7.49 (t, J=8.0 Hz, 1H), 7.37-7.27 (m, 6H), 4.17-4.12 (m, 2H), 3.51 (dd, J=9.1, 4.1 Hz, 1H), 3.36 (s, 2H), 3.35 (dd, J=14.1, 4.3 Hz, 1H), 2.92 (dd, J=14.1, 9.0 Hz, 1H), 1.22 (t, J=7.2 Hz, 3H).

Workup

  1. customThe crude product was purified

Sources & evidence

ORD record
ord-944df10b03d845fab197b17206f2c7c1
Source dataset
uspto-grants-2014_07
Patent number
US08785468B2

Reaction notes

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