3-(Methylsulfonyl)phenylboronic acid → 4-amino-8-(3-methylsulfonylphenyl)-N-propyl-cinnoline-3-carboxamide

HRID 31097Notes

Reaction equation

HRID 31097 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][S:20]([C:23]1[CH:24]=[C:25](B(O)O)[CH:26]=[CH:27][CH:28]=1)(=[O:22])=[O:21]>>[NH2:1][C:2]1[C:11]2[C:6](=[C:7]([C:27]3[CH:26]=[CH:25][CH:24]=[C:23]([S:20]([CH3:19])(=[O:22])=[O:21])[CH:28]=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 27735423-(Methylsulfonyl)phenylboronic acidHCID 140123264-Amino-8-bromo-N-propylcinnoline-3-carboxamide

Product 1

HCID 236301394-amino-8-(3-methylsulfonylphenyl)-N-propyl-cinnoline-3-carboxamideYield 83.1%

Procedure

Using method A, 4-amino-8-bromo-N-propyl-cinnoline-3-carboxamide (150 mg, 0.485 mmol) and 3-(methylsulfonyl)phenylboronic acid (200 mg, 1.000 mmol) were reacted to afford the title compound (155 mg, 83% yield) as a white solid. 1H NMR (300 MHz, CDCl3) δ 8.51 (br, 1H), 8.21 (m, 1H), 8.11-7.67 (m, 6H), 3.45 (apparent quartet, J=7.0 Hz, 2H), 3.12 (s, 3H), 1.67 (apparent sextet, J=7.0 Hz, 2H), 1.01 (t, J=7.0 Hz, 3H). MS APCI, m/z=385 (M+H) HPLC 1.75 min.

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-f5bacc6cc8e745ec978efcebaccdec69
Source dataset
uspto-grants-2008_09
Patent number
US07425556B2

Reaction notes

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