4-Amino-8-bromo-N-propylcinnoline-3-carboxamide → HCID 25133109, compound

HRID 2375662Notes

Reaction equation

HRID 2375662 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[CH:22]=[CH:23][C:24]([CH3:30])=[C:25](B(O)O)[CH:26]=1>>[NH2:1][C:2]1[C:11]2[C:6](=[C:7]([C:23]3[CH:22]=[C:21]([O:20][CH3:19])[CH:26]=[CH:25][C:24]=3[CH3:30])[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 140123264-Amino-8-bromo-N-propylcinnoline-3-carboxamideHCID 17750868(5-Methoxy-2-methylphenyl)boronic acid

Product 1

HCID 25133109HCID 25133109, compoundYield 73.6%

Procedure

Using method A, 4-amino-8-bromo-N-propyl-cinnoline-3-carboxamide (150 mg, 0.485 mmol) and 5-methoxy-2-methyl-phenylboronic acid (125 mg, 1.000 mmol) were reacted to afford the title compound (125 mg, 73% yield). 1H NMR (300 MHz, CDCl3) δ 8.55 (br, 1H), 7.88 (m, 1H), 7.76-7.64 (m, 2H), 7.21 (m, 1H), 6.92-6.81 (m, 2H), 3.79 (s, 3H), 3.45 (apparent quartet, J=7.0 Hz, 2H), 1.97 (s, 3H), 1.65 (apparent sextet, J=7.0 Hz, 2H), 0.99 (t, J=7.0 Hz, 3H). MS APCI, m/z=351 (M+H). HPLC 1.77 min.

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-375f7df44ebf48b199afc2397e2c16b6
Source dataset
uspto-grants-2008_12
Patent number
US07465795B2

Reaction notes

Loading…