(2,4-Dimethoxypyrimidin-5-yl)boronic acid → HCID 23629960, compound

HRID 2375596Notes

Reaction equation

HRID 2375596 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[C:7](Br)[CH:8]=[CH:9][CH:10]=2)[N:5]=[N:4][C:3]=1[C:13]([NH:15][CH2:16][CH2:17][CH3:18])=[O:14].[CH3:19][O:20][C:21]1[N:26]=[C:25]([O:27][CH3:28])[C:24](B(O)O)=[CH:23][N:22]=1>>[NH2:1][C:2]1[C:11]2[C:6](=[C:7]([C:24]3[C:25]([O:27][CH3:28])=[N:26][C:21]([O:20][CH3:19])=[N:22][CH:23]=3)[CH:8]=[CH:9][CH:10]=2)[N:5]=[N:4][C:3]=1[C:13]([NH:15][CH2:16][CH2:17][CH3:18])=[O:14]

Participants

3

Reactant 2

HCID 2736209(2,4-Dimethoxypyrimidin-5-yl)boronic acidHCID 140123264-Amino-8-bromo-N-propylcinnoline-3-carboxamide

Product 1

HCID 23629960HCID 23629960, compoundYield 28%

Procedure

Using method A, 4-amino-8-bromo-N-propyl-cinnoline-3-carboxamide (100 mg, 0.324 mmol) and (2,4-dimethoxypyrimidin-5-yl)boronic acid (125 mg, 0.68 mmol) were reacted to afford the title compound (33 mg, 28% yield) as a white solid. 1H NMR (300 MHz, CDCl3) δ 8.52 (bm, 1H), 8.33 (s, 1H), 7.91 (dd, J=7.7, 2.0 Hz, 1H), 7.70-7.77 (m, 2H), 4.06 (s, 3H), 3.93 (s, 3H), 3.46 (apparent q, J=6.5 Hz, 2H), 1.67 (apparent sextet, J=7.2 Hz, 2H), 1.00 (t, J=7.4 Hz, 3H). MS APCI, m/z=369 (M+H) HPLC 1.69 min.

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-1135754fc883440f91fbbfb051599533
Source dataset
uspto-grants-2008_12
Patent number
US07465795B2

Reaction notes

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