2,4-Dimethoxybenzeneboronic acid → HCID 59791617, compound

HRID 2375697Notes

Reaction equation

HRID 2375697 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[CH:28]=[C:27]([O:29][CH3:30])[CH:26]=[CH:25][C:24]=1B(O)O>>[NH2:1][C:2]1[C:11]2[C:6](=[C:7]([C:26]3[CH:25]=[CH:24][C:23]([O:22][CH3:21])=[CH:28][C:27]=3[O:29][CH3:30])[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 27343412,4-Dimethoxybenzeneboronic acidHCID 672297344-amino-8-bromo-7-fluoro-N-cyclobutyl-cinnoline-3-carboxamide

Product 1

HCID 59791617HCID 59791617, compoundYield 65%

Procedure

Using Method A, 4-amino-8-bromo-7-fluoro-N-cyclobutyl-cinnoline-3-carboxamide (175 mg) and 2,4-dimethoxy-phenyl boronic acid (205 mg) were reacted to afford the title compound (133 mg) as white solid. 1H NMR (500 MHz, DMSO-d6) δ 9.20 (d, 1H), 8.47 (m, 1H), 7.70 (m, 1H), 7.18 (m, 1H), 6.70 (m, 1H), 6.64 (m, 1H), 4.49 (m, 1H), 3.85 (s, 3H), 3.65 (s, 3H), 2.26-2.10(m, 4H), 1.72-1.62 (m, 2H). MS APCI, m/z=397 (M+H).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-0703f90e996945dd86db56865bb59ae1
Source dataset
uspto-grants-2008_12
Patent number
US07465795B2

Reaction notes

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