2-(Bromomethyl)benzonitrile → HCID 58168102, compound

HRID 1029283Notes

Reaction equation

HRID 1029283 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.Br[CH2:18][C:19]1[CH:26]=[CH:25][CH:24]=[CH:23][C:20]=1[C:21]#[N:22]>>[O:14]=[C:6]1[C:5]2[CH:15]=[CH:16][C:2]([NH:1][CH2:18][C:19]3[CH:26]=[CH:25][CH:24]=[CH:23][C:20]=3[C:21]#[N:22])=[CH:3][C:4]=2[C:13]2[C:8](=[N:9][CH:10]=[CH:11][CH:12]=2)[NH:7]1

Participants

3

Reactant 2

HCID 895992-(Bromomethyl)benzonitrileHCID 581679519-amino-5H-benzo[c][1,8]naphthyridin-6-one

Product 1

HCID 58168102HCID 58168102, compoundYield 21%

Procedure

The title compound was synthesized according to the procedure described for the preparation of Example 458 using 70 (140 mg, 0.66 mmol) and 2-(bromomethyl)benzonitrile (156 mg, 0.80 mmol) to provide 462 (45 mg, 21% yield) as a white powder. LC-MS (M+H=327, obsd.=327). 1H NMR (400 MHz, DMSO-D6) δ 8.56 (dd, J=1.6, 8.0, 1H), 8.47 (dd, J=1.6, 4.7, 1H), 8.06 (d, J=8.7, 1H), 7.87 (dd, J=1.2, 7.7, 1H), 7.47 (m, 1H), 7.41 (m, 1H), 7.40 (d, J=7.7, 1H), 7.36 (dd, J=4.7, 7.9, 1H), 6.98 (d, J=7.9, 1H), 6.91 (dd, J=2.0, 8.7, 1H), 6.25 (s, 1H), 5.81 (s, 2H).

Workup

  1. customThe title compound was synthesized

Sources & evidence

ORD record
ord-8ac091ac65be4660b31c195e35df44b7
Source dataset
uspto-grants-2014_05
Patent number
US08735584B2

Reaction notes

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