2,5-Dimethoxyphenylboronic acid → HCID 54581332, compound

HRID 2375683Notes

Reaction equation

HRID 2375683 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][CH:16]1[CH2:18][CH2:17]1)=[O:14].[CH3:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][C:22]=1B(O)O>>[NH2:1][C:2]1[C:11]2[C:6](=[C:7]([C:25]3[CH:26]=[C:21]([O:20][CH3:19])[CH:22]=[CH:23][C:24]=3[O:27][CH3:28])[CH:8]=[CH:9][CH:10]=2)[N:5]=[N:4][C:3]=1[C:13]([NH:15][CH:16]1[CH2:18][CH2:17]1)=[O:14]

Participants

3

Reactant 2

HCID 27343422,5-Dimethoxyphenylboronic acidHCID 672292774-amino-8-bromo-N-cyclopropylcinnoline-3-carboxamide

Product 1

HCID 54581332HCID 54581332, compoundYield 85%

Procedure

Using Method A, 4-amino-8-bromo-N-cyclopropyl-cinnoline-3-carboxamide (100 mg, 0.33 mmol) and 2,5-dimethoxyphenylboronic acid (118 mg, 0.65 mmol) were reacted. After purification the title compound (101 mg, 85% yield) was obtained as a white solid. 1H NMR (300 MHz, CDCl3) δ 8.56 (bm, 1H), 7.85 (a dd, J=2.2, 7.6 Hz, 1H), 7.73 (m, 2H), 6.95 (m, 2H), 6.91 (m, 1H), 3.77 (s, 3H), 3.63 (s, 3H), 2.96 (m, 1H), 0.88 (m, 2H), 0.65 (m, 2H). MS APCI, m/z=365, HPLC 2.42 min.

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-7efbc6d0c7a74cf099328d08f8a996fb
Source dataset
uspto-grants-2008_12
Patent number
US07465795B2

Reaction notes

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