Benzonitrile, 3-(bromomethyl)- → HCID 58168231, compound

HRID 1029284Notes

Reaction equation

HRID 1029284 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:20]=[C:21]([CH:24]=[CH:25][CH:26]=1)[C:22]#[N:23]>>[O:14]=[C:6]1[C:5]2[CH:15]=[CH:16][C:2]([NH:1][CH2:18][C:19]3[CH:20]=[C:21]([CH:24]=[CH:25][CH:26]=3)[C:22]#[N:23])=[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 97249Benzonitrile, 3-(bromomethyl)-HCID 581679519-amino-5H-benzo[c][1,8]naphthyridin-6-one

Product 1

HCID 58168231HCID 58168231, compoundYield 16%

Procedure

The title compound was synthesized according to the procedure described for the preparation of Example 458 using 70 (141 mg, 0.67 mmol) and 3-(bromo methyl)benzonitrile (157 mg, 0.80 mmol) to provide 463 (35 mg, 16% yield) as a white powder. LC-MS (M+H=327, obsd.=327). 1H NMR (400 MHz, DMSO-D6) δ 8.46 (m, 2H), 8.06 (d, J=8.6, 1H), 7.73 (s, 1H), 7.69 (d, J=7.6, 1H), 7.57 (d, J=8.0, 1H), 7.48 (t, J=7.8, 1H), 7.42 (d, J=2.0, 1H), 7.36 (dd, J=4.7, 7.8, 1H), 6.90 (dd, J=2.1, 8.7, 1H), 6.22 (s, 2H), 5.69 (s, 2H).

Workup

  1. customThe title compound was synthesized

Sources & evidence

ORD record
ord-4325d0b7f2fc4bcc9f618d13703433d7
Source dataset
uspto-grants-2014_05
Patent number
US08735584B2

Reaction notes

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