3-(Dimethylamino)benzeneboronic acid → HCID 23630066, compound

HRID 2375622Notes

Reaction equation

HRID 2375622 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][N:20]([CH3:30])[C:21]1[CH:22]=[C:23](B(O)O)[CH:24]=[CH:25][CH:26]=1>>[NH2:1][C:2]1[C:11]2[C:6](=[C:7]([C:25]3[CH:24]=[CH:23][CH:22]=[C:21]([N:20]([CH3:30])[CH3:19])[CH:26]=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 27625273-(Dimethylamino)benzeneboronic acidHCID 140123264-Amino-8-bromo-N-propylcinnoline-3-carboxamide

Product 1

HCID 23630066HCID 23630066, compoundYield 88.6%

Procedure

Using method A, 4-amino-8-bromo-N-propyl-cinnoline-3-carboxamide (100 mg, 0.33 mmol) and 3-dimethylaminophenyl boronic acid (160 mg, 0.97 mmol) were reacted to afford the title compound (99 mg, 88.6% yield) as a pale-yellow solid. 1H NMR (300 MHz, CDCl3) δ 8.60 (br, 1H), 7.83 (m, 2H), 7.70 (t, J=7.7 Hz, 1H), 7.35 (t, J=7.9 Hz, 1H), 7.03 (d, J=7.9 Hz, 1H), 6.98 (m, 1H), 6.82 (dd, J=8.3 Hz, J′=2.3 Hz, 1H), 3.46 (q, J=6.7 Hz, 2H), 2.99 (s, 6H), 1.67 (m, J=7.2 Hz, 2H), 1.00 (t, J=7.4 Hz, 3H) MS APCI, m/z=350 (M+H) HPLC 1.60 min.

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-49cfdf8e89dd4bc6be35706790d453f8
Source dataset
uspto-grants-2008_12
Patent number
US07465795B2

Reaction notes

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