O-Toluidine → HCID 58168339, compound

HRID 1029203Notes

Reaction equation

HRID 1029203 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.[NH2:17][C:18]1[C:19]([CH3:24])=[CH:20][CH:21]=[CH:22][CH:23]=1>>[C:19]1([CH3:24])[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[NH:17][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

Participants

3

Reactant 2

HCID 7242O-ToluidineHCID 581682989-chloro-5H-benzo[c][1,8]naphthyridin-6-one

Product 1

HCID 58168339HCID 58168339, compoundYield 23.9%

Procedure

The title compound was synthesized according to the procedure described for the preparation of Example 231 using 6 (100 mg, 0.43 mmol) and o-toluidine (0.07 mL, 0.65 mmol) to provide 240 (31 mg, 21% yield) as a yellow/green powder. LC-MS (M+H (parent)=302, obsd.=302). 1H NMR (400 MHz, d6-DMSO): δ 11.63 (s, 1H), 8.44 (dd, 1H), 8.37 (s, 1H), 8.33 (dd, 1H), 8.10 (d, 1H), 7.55 (d, 1H), 7.33 (m, 2H), 7.25 (m, 2H), 7.11 (m, 1H), 7.07 (dd, 1H), 2.24 (s, 3H).

Workup

  1. customThe title compound was synthesized

Sources & evidence

ORD record
ord-76c2d2e57fcb4ad097572bf25f163364
Source dataset
uspto-grants-2014_05
Patent number
US08735584B2

Reaction notes

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