Hydrochloric Acid → HCID 57691358, compound

HRID 219199Notes

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-53c0c299a37646908fb69e75a8261c6e
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08198448B2

Reaction notes

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