Hydrochloric Acid → 6-((6-Phenyl-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methyl)quinolin-3-ol

HRID 219196Notes

Reaction equation

HRID 219196 reaction equation
C[O:2][C:3]1[CH:4]=[N:5][C:6]2[C:11]([CH:12]=1)=[CH:10][C:9]([CH2:13][C:14](OC(C)(C)C)=O)=[CH:8][CH:7]=2.[C:21]1([C:27]2[N:32]=[N:31][C:30]([NH:33][NH2:34])=[CH:29][CH:28]=2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.Cl.[OH-].[Na+]>>[C:21]1([C:27]2[CH:28]=[CH:29][C:30]3[N:31]([C:14]([CH2:13][C:9]4[CH:10]=[C:11]5[C:6](=[CH:7][CH:8]=4)[N:5]=[CH:4][C:3]([OH:2])=[CH:12]5)=[N:34][N:33]=3)[N:32]=2)[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 64098423-Hydrazinyl-6-phenylpyridazineHCID 59843087Tert-butyl 2-(3-methoxyquinolin-6-yl)acetate

Product 1

HCID 576913296-((6-Phenyl-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methyl)quinolin-3-ol

Conditions

Temperature
100 °C

Procedure

To a 5 ml CEM microwave tube was added tert-butyl 2-(3-methoxyquinolin-6-yl)acetate (0.3 g, 1 mmol), 1-(6-phenylpyridazin-3-yl)hydrazine (0.3 g, 2 mmol), and HYDROCHLORIC ACID (0.3 ml, 11 mmol) as solvent. The vial was sealed and first heated at 100° C. for 20 min then placed into CEM microwave for 20 min. at 180° C., with 100 Watts of power via Powermax. The reaction mixture was adjusted the pH to 7 by adding 5 N NaOH. The ppt. was collected by filtration. The ppt. was washed with water and dried. The solid was purified using SiO2 chromatography (TELEDYNE ISCO REDISEP®, P/N 68-2203-027, 40 g SiO2, DCM:MeOH=95%:5%, Flow=40 mL/min) to afford the desired product as gray solid. MS m/z: 354.2 (M+H). Calc'd. for C21H15N5O−353.37.

Workup

  1. customThe vial was sealed
  2. filtrationwas collected by filtration
  3. washwas washed with water
  4. customdried
  5. customThe solid was purified

Sources & evidence

ORD record
ord-417b5b2e68c14c8698223ef56d332f2a
Source dataset
uspto-grants-2012_06
Patent number
US08198448B2

Reaction notes

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