3-Aminopyridine → 1-chloro-9-(1-methyl-1H-pyrazol-4-yl)-N-pyridin-3-ylbenzo[c]-1,6-naphthyridin-6-amine

HRID 2192967Notes

Reaction equation

[Cl:1][C:2]1[N:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4]1[CH:16]=[C:15]([C:17]3[CH:18]=[N:19][N:20]([CH3:22])[CH:21]=3)[CH:14]=[CH:13][C:5]=1[C:6](Cl)=[N:7]2.[NH2:23][C:24]1[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=1.CC(C)([O-])C.[Na+].[Cl-].[NH4+]>C1COCC1.C(OCC)(=O)C>[Cl:1][C:2]1[N:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4]1[CH:16]=[C:15]([C:17]3[CH:18]=[N:19][N:20]([CH3:22])[CH:21]=3)[CH:14]=[CH:13][C:5]=1[C:6]([NH:23][C:24]1[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=1)=[N:7]2

Participants

Conditions

Temperature: 85 °C

Procedure

To a solution of 1,6-dichloro-9-(1-methyl-1H-pyrazol-4-yl)benzo[c]-1,6-naphthyridine (50 mg, 0.152 mmol) and 3-aminopyridine (14.30 mg, 0.152 mmol) in THF (1.5 mL), sodium tert-butoxide (43.8 mg, 0.456 mmol) was added. The reaction mixture was heated to 85° C. for 1 h. After cooling to room temperature, aqueous ammonium chloride (saturated) and ethyl acetate were added. The mixture was extracted with ethyl acetate. The combined organic extracts were dried over sodium sulfate and concentrated under reduced pressure to afford 1-chloro-9-(1-methyl-1H-pyrazol-4-yl)-N-pyridin-3-ylbenzo[c]-1,6-naphthyridin-6-amine as a yellow solid. LRMS (APCI) calc'd for (C21H15ClN6) [M+H]+, 387.1; found 387.1.

Workup

temperatureAfter cooling to room temperature
extractionThe mixture was extracted with ethyl acetate
dry with materialThe combined organic extracts were dried over sodium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-a22ab14a53d7405c8e25948fdc688ff7
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08329722B2

Reaction notes

Loading…