Benzene, 1-(bromomethyl)-3-nitro- → HCID 58168260, compound

HRID 1029285Notes

Reaction equation

HRID 1029285 reaction equation
[NH2:1][C:2]1[CH:16]=[CH:15][C:5]2[C:6](=[O:14])[NH:7][C:8]3[C:13]([C:4]=2[CH:3]=1)=[CH:12][CH:11]=[CH:10][N:9]=3.[N+:17]([C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][CH:27]=1)[CH2:23]Br)([O-:19])=[O:18]>>[N+:17]([C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][CH:27]=1)[CH2:23][NH:1][C:2]1[CH:16]=[CH:15][C:5]2[C:6](=[O:14])[NH:7][C:8]3[C:13]([C:4]=2[CH:3]=1)=[CH:12][CH:11]=[CH:10][N:9]=3)([O-:19])=[O:18]

Participants

3

Reactant 2

HCID 77568Benzene, 1-(bromomethyl)-3-nitro-HCID 581679519-amino-5H-benzo[c][1,8]naphthyridin-6-one

Product 1

HCID 58168260HCID 58168260, compoundYield 11.5%

Procedure

The title compound was synthesized according to the procedure described for the preparation of Example 458 using 70 (115 mg, 0.55 mmol) and 3-nitro-benzyl bromide (113 mg, 0.66 mmol) to provide 465 (22 mg, 11% yield) as a white powder. LC-MS (M+H=347, obsd.=347). 1H NMR (400 MHz, DMSO-D6) δ 8.47 (m, 2H), 8.13 (s, 1H), 8.05 (m, 2H), 7.74 (d, J=7.7 , 1H), 7.58 (t, J=7.9, 1H), 7.42 (d, J=2.0, 1H), 7.37 (dd, J=4.7, 7.8, 1H), 6.91 (dd, J=2.0, 8.7, 1H), 6.24 (s, 2H), 5.76 (s, 2H).

Workup

  1. customThe title compound was synthesized

Sources & evidence

ORD record
ord-80144e312c51492fb9d70773959ab5cb
Source dataset
uspto-grants-2014_05
Patent number
US08735584B2

Reaction notes

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