p-Toluenesulfonic acid monohydrate → 7-Methoxy-4-(2-(6-phenyl-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)ethyl)quinoline

HRID 40183

Reaction equation

HRID 40183 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([CH2:13][CH2:14][C:15](OCC)=O)=[CH:8][CH:9]=[N:10]2)=[CH:5][CH:4]=1.[C:20]1([C:26]2[N:31]=[N:30][C:29]([NH:32][NH2:33])=[CH:28][CH:27]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.CC1C=CC(S(O)(=O)=O)=CC=1.O>CS(C)=O>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([CH2:13][CH2:14][C:15]3[N:30]4[N:31]=[C:26]([C:20]5[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=5)[CH:27]=[CH:28][C:29]4=[N:32][N:33]=3)=[CH:8][CH:9]=[N:10]2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 521998p-Toluenesulfonic acid monohydrateHCID 64098423-Hydrazinyl-6-phenylpyridazineHCID 67503802Ethyl 3-(7-methoxyquinolin-4-yl)propanoate

Product 1

HCID 250669887-Methoxy-4-(2-(6-phenyl-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)ethyl)quinoline

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Ethyl 3-(7-methoxyquinolin-4-yl)propanoate (156 mg, 0.60 mmol) was combined with 1-(6-phenylpyridazin-3-yl)hydrazine (115 mg, 0.62 mmol) and pTsOH.H2O(140 mg, 0.72 mmol). The mixture was microwaved at 150° C. for 60 minutes. The residue was taken up in DMSO and purified by HPLC and neutralized to yield the desired product as an off-white solid. (ESI, pos. ion) m/z: 382.1 (M+H).

Workup

  1. customThe mixture was microwaved at 150° C. for 60 minutes
  2. custompurified by HPLC

Sources & evidence

ORD record
ord-31f20ad462494b188d876dc5a7c25daa
Source dataset
uspto-grants-2013_09
Patent number
US08524900B2

Linked notes

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