Hydrochloric Acid → HCID 57691358, compound

HRID 40305Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[N:5][C:6]2[C:11]([CH:12]=1)=[CH:10][C:9]([CH:13]([CH3:21])[C:14](OC(C)(C)C)=O)=[CH:8][CH:7]=2.[C:22]1([C:28]2[N:33]=[N:32][C:31]([NH:34][NH2:35])=[CH:30][CH:29]=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.Cl.[OH-].[Na+]>O>[CH3:1][O:2][C:3]1[CH:4]=[N:5][C:6]2[C:11]([CH:12]=1)=[CH:10][C:9]([CH:13]([C:14]1[N:32]3[N:33]=[C:28]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[CH:29]=[CH:30][C:31]3=[N:34][N:35]=1)[CH3:21])=[CH:8][CH:7]=2

Participants

Conditions

Temperature: 90 °C

Procedure

To a 5 ml CEM microwave tube was added tert-butyl 2-(3-methoxyquinolin-6-yl)propanoate (0.130 g, 0.45 mmol), 1-(6-phenylpyridazin-3-yl)hydrazine (0.17 g, 0.90 mmol), HYDROCHLORIC ACID (0.11 ml, 1.4 mmol), and water (0.2 mL) as solvent. The vial was sealed and first heated at 90° C. for 30 min then placed into CEM microwave for 15 min. at 140° C., with 100 Watts of power via Powermax. The reaction mixture was adjusted the pH to 7 by adding 5 N NaOH and the solid was collected by filtration. The brown ppt. was dissolved in DCM. The organic was washed with water, dried over MgSO4, and removed solvent in vacuo. The crude product was purified using SiO2 chromatography (Teledyne Isco RediSep®, P/N 68-2203-027, 40 g SiO2, DCM:MeOH=97%:3%, Flow=40 mL/min) to afford the desired product as light yellowish solid. MS m/z: 382.3 (M+H). Calc'd. for C23H19N5O—381.43.

Workup

customThe vial was sealed
filtrationthe solid was collected by filtration
dissolutionwas dissolved in DCM
washThe organic was washed with water
dry with materialdried over MgSO4
customremoved solvent in vacuo
customThe crude product was purified

Sources & evidence

ORD record: ord-d7d21f9550da4c43a7365a99867a7d89
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08524900B2

Reaction notes

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