(2,4-Dimethoxypyrimidin-5-yl)boronic acid → HCID 23629829, compound

HRID 2375698Notes

Reaction equation

HRID 2375698 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[C:7](Br)[C:8]([F:12])=[CH:9][CH:10]=2)[N:5]=[N:4][C:3]=1[C:14]([NH:16][CH:17]1[CH2:20][CH2:19][CH2:18]1)=[O:15].[CH3:21][O:22][C:23]1[N:28]=[C:27]([O:29][CH3:30])[C:26](B(O)O)=[CH:25][N:24]=1>>[NH2:1][C:2]1[C:11]2[C:6](=[C:7]([C:26]3[C:27]([O:29][CH3:30])=[N:28][C:23]([O:22][CH3:21])=[N:24][CH:25]=3)[C:8]([F:12])=[CH:9][CH:10]=2)[N:5]=[N:4][C:3]=1[C:14]([NH:16][CH:17]1[CH2:20][CH2:19][CH2:18]1)=[O:15]

Participants

3

Reactant 2

HCID 2736209(2,4-Dimethoxypyrimidin-5-yl)boronic acidHCID 672297344-amino-8-bromo-7-fluoro-N-cyclobutyl-cinnoline-3-carboxamide

Product 1

HCID 23629829HCID 23629829, compoundYield 42.8%

Procedure

Using Method A, 4-amino-8-bromo-7-fluoro-N-cyclobutyl-cinnoline-3-carboxamide (175 mg) and 2,4-dimethoxypyrimidin-5-yl boronic acid (207 mg) were reacted to afford the title compound (88 mg) as white solid. 1H NMR (500 MHz, DMSO-d6) δ 9.24 (d, 1H), 8.57 (m, 1H), 8.38 (s, 1H), 7.77 (m, 1H), 4.49 (m, 1H), 4.00 (s, 3H), 3.84 (s, 3H), 2.26-2.10(m, 4H), 1.72-1.62 (m, 2H). MS APCI, m/z=399 (M+H).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-423099ba84ff4d8291b992782d713043
Source dataset
uspto-grants-2008_12
Patent number
US07465795B2

Reaction notes

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