4-Chlorobenzylamine → HCID 58168303, compound

HRID 1029273Notes

Reaction equation

Cl[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.[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][NH2:25])=[CH:20][CH:19]=1>>[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][NH:25][C:2]2[CH:16]=[CH:15][C:5]3[C:6](=[O:14])[NH:7][C:8]4[C:13]([C:4]=3[CH:3]=2)=[CH:12][CH:11]=[CH:10][N:9]=4)=[CH:20][CH:19]=1

Participants

Reactant 2

HCID 660364-Chlorobenzylamine

HCID 581682989-chloro-5H-benzo[c][1,8]naphthyridin-6-one

Product 1

HCID 58168303HCID 58168303, compoundYield 14%

Procedure

The title compound was synthesized according to the procedure described for the preparation of Example 448 using 6 (100 mg, 0.43 mmol) and (4-chloro-phenyl)methanamine (245 mg, 1.73 mmol) to provide 452 (20 mg, 14% yield) as a white powder. LC-MS (M+H=337, obsd.=337). 1H NMR (400 MHz, DMSO-D6) δ 11.49 (s, 1H), 8.56 (d, J=8.3, 1H), 8.41 (s, 1H), 7.99 (d, J=8.8, 1H), 7.44 (dd, J=8.5, 22.3, 2H), 7.37 (s, 2H), 7.25 (d, J=12.5, 2H), 6.95 (s, 1H), 4.51 (s, 2H).

Workup

customThe title compound was synthesized

Sources & evidence

ORD record: ord-fabde9a9b02c49428f23f22e12eab51d
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08735584B2

Reaction notes

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