Potassium Carbonate → 3-(5-amino-2-methyl-phenyl)-7-chloro-1-phenyl-1H-[1,6]naphthyridin-2-one

HRID 424707Notes

Reaction equation

[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]=O)=[C:4]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:3]=1.[NH2:17][C:18]1[CH:19]=[CH:20][C:21]([CH3:29])=[C:22]([CH2:24][C:25]([O:27]C)=[O:26])[CH:23]=1.[C:30](=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[NH2:17][C:18]1[CH:19]=[CH:20][C:21]([CH3:29])=[C:22]([C:24]2[C:25](=[O:26])[N:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:4]3[C:5]([CH:8]=2)=[CH:6][N:7]=[C:2]([CH3:30])[CH:3]=3)[CH:23]=1.[NH2:17][C:18]1[CH:19]=[CH:20][C:21]([CH3:29])=[C:22]([C:24]2[C:25](=[O:27])[N:10]([C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:4]3[C:5]([CH:8]=2)=[CH:6][N:7]=[C:2]([Cl:1])[CH:3]=3)[CH:23]=1

Participants

Conditions

Temperature: 100 °C

Procedure

6-Chloro-4-phenylamino-pyridine-3-carbaldehyde 18 (21 mg, 0.09 mmol) is mixed with 2-(5-amino-2-methyl-phenyl)acetic acid methyl ester 7 (18 mg, 0.1 mmol) and potassium carbonate (37 mg, 0.27 mmol) in DMF (2 mL). The mixture is heated to 100° C. for 16 h. After cooling to rt and removing solvent in vacuo, the crude product is purified using flash chromatography (hexane:ethyl acetate=1:1). The title compound 3-(5-amino-2-methyl-phenyl)-7-chloro-1-phenyl-1H-[1,6]naphthyridin-2-one 19 is obtained as a pale solid. 1H NMR (400 MHz, CDCl3) δ 8.53 (s, 1H), 7.68 (s, 1H), 7.53-7.57 (m, 2H), 7.47-7.51 (dt 1H), 7.20-7.23 (m, 2H), 6.96 (d, 1H), 6.59 (dd, 1H), 6.58 (s, 1H), 6.52 (s, 1H), 2.05 (s, 3H).

Workup

temperatureAfter cooling to rt
customremoving solvent in vacuo
customthe crude product is purified

Sources & evidence

ORD record: ord-5b2be7e8f44c4ccb8b8cfd1fa1983664
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08106068B2

Reaction notes

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