p-Toluidine → HCID 58168258, compound

HRID 1029201Notes

Reaction equation

HRID 1029201 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[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=1>>[C:21]1([CH3:24])[CH:22]=[CH:23][C:18]([NH:17][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:19][CH:20]=1

Participants

3

Reactant 2

HCID 7813p-ToluidineHCID 581682989-chloro-5H-benzo[c][1,8]naphthyridin-6-one

Product 1

HCID 58168258HCID 58168258, compoundYield 21.1%

Procedure

The title compound was synthesized according to the procedure described for the preparation of Example 231 using 6 (50 mg, 0.22 mmol) and p-toluidine (35 mg, 0.33 mmol) to provide 238 (14 mg, 21% yield) as a black solid. LC-MS (M+H=302, obsd.=302). 1H NMR (400 MHz, d6-DMSO): δ 11.64 (s, 1H), 8.82 (s, 1H), 8.44 (m, 2H), 8.12 (d, 1H), 7.78 (d, 1H), 7.27 (m, 1H), 7.22 (dd, 1H), 7.19 (s, 3H), 2.30 (s, 4H).

Workup

  1. customThe title compound was synthesized

Sources & evidence

ORD record
ord-5cd99c79444c4bdfb514584e4d300a08
Source dataset
uspto-grants-2014_05
Patent number
US08735584B2

Reaction notes

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