(Pyrimidin-5-yl)boronic acid → HCID 178461423, compound

HRID 2047515Notes

Reaction equation

HRID 2047515 reaction equation
Br[C:2]1[CH:20]=[CH:19][C:5]2[N:6]=[C:7]([C@H:9]3[CH2:12][C@H:11]([N:13]4[CH2:17][CH2:16][CH2:15][C@H:14]4[CH3:18])[CH2:10]3)[S:8][C:4]=2[CH:3]=1.CC1(C)C(C)(C)OB([C:29]2[CH:30]=[N:31][C:32]3[C:37]([CH:38]=2)=[CH:36][CH:35]=[CH:34][CH:33]=3)O1.N1C=C(B(O)O)C=NC=1>>[CH3:18][C@H:14]1[CH2:15][CH2:16][CH2:17][N:13]1[C@H:11]1[CH2:12][C@H:9]([C:7]2[S:8][C:4]3[CH:3]=[C:2]([C:29]4[CH:30]=[N:31][C:32]5[C:37]([CH:38]=4)=[CH:36][CH:35]=[CH:34][CH:33]=5)[CH:20]=[CH:19][C:5]=3[N:6]=2)[CH2:10]1

Participants

4

Reactant 3

HCID 2795193(Pyrimidin-5-yl)boronic acidHCID 108485903-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)quinolineHCID 178461421HCID 178461421, compound

Product 1

HCID 178461423HCID 178461423, compound

Procedure

The title compound was prepared according to the procedure described in Example 1F, substituting the product of Example 11A for the product of Example 1E and substituting 3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-quinoline for pyrimidine-5-boronic acid. 1H NMR (500 MHz, CDCl3) δ ppm 9.24 (d, J=2.50 Hz, 1H) 8.37 (d, J=2.50 Hz, 1H) 8.09-8.21 (m, 3H) 7.90 (d, J=8.11 Hz, 1H) 7.81 (dd, J=8.42, 1.87 Hz, 1H) 7.71-7.78 (m, 1H) 7.54-7.66 (m, 1H) 3.82-3.99 (m, 1H) 3.46-3.64 (m, 1H) 2.98-3.16 (m, 1H) 2.65-2.86 (m, 2H) 2.42-2.64 (m, 2H) 2.28-2.41 (m, 1H) 1.92-2.05 (m, 1H) 1.81-1.89 (m, 1H) 1.69-1.78 (m, 1H) 1.44-1.63 (m, 2H) 1.16 (s, 3H). MS: (M+H)+=400.

Sources & evidence

ORD record
ord-e1498c660c5245f197fd0955aa34de71
Source dataset
uspto-grants-2013_11
Patent number
US08592467B2

Reaction notes

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