Hydrochloric Acid → 3-[3-(3-{[(Methylamino)carbonyl]amino]phenyl)imidazo[1,2-b]pyridazin-7-yl]benzoic acid

HRID 407082Notes

Reaction equation

HRID 407082 reaction equation
O.[OH-].[Li+].[CH3:4][NH:5][C:6]([NH:8][C:9]1[CH:10]=[C:11]([C:15]2[N:19]3[N:20]=[CH:21][C:22]([C:24]4[CH:25]=[C:26]([CH:31]=[CH:32][CH:33]=4)[C:27]([O:29]C)=[O:28])=[CH:23][C:18]3=[N:17][CH:16]=2)[CH:12]=[CH:13][CH:14]=1)=[O:7].C1COCC1.Cl>CO.O>[CH3:4][NH:5][C:6]([NH:8][C:9]1[CH:10]=[C:11]([C:15]2[N:19]3[N:20]=[CH:21][C:22]([C:24]4[CH:25]=[C:26]([CH:31]=[CH:32][CH:33]=4)[C:27]([OH:29])=[O:28])=[CH:23][C:18]3=[N:17][CH:16]=2)[CH:12]=[CH:13][CH:14]=1)=[O:7]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 67980168Methyl 3-[3-(3-{[(methylamino)carbonyl]amino}phenyl)imidazo[1,2-b]pyridazin-7-yl]benzoate

Product 1

HCID 679800673-[3-(3-{[(Methylamino)carbonyl]amino]phenyl)imidazo[1,2-b]pyridazin-7-yl]benzoic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Lithium hydroxide, monohydrate (89 mg, 2.1 mmol) was added to a mixture of methyl 3-[3-(3-{[(methylamino)carbonyl]amino}phenyl)imidazo[1,2-b]pyridazin-7-yl]benzoate (0.17 g, 0.43 mmol) in methanol (4.0 mL)/THF (2.0 mL)/water (1 mL) and then the reaction was stirred at r.t. for 4 h. The mixture was adjusted with conc. HCl to PH˜3. The volatiles were removed under reduced pressure to provide the crude product which was directly used in the next step without further purification. LCMS (M+H)+: m/z=388.1

Workup

  1. customThe volatiles were removed under reduced pressure

Sources & evidence

ORD record
ord-89b4922497d14ad88fdc6bbc2142a604
Source dataset
uspto-grants-2014_06
Patent number
US08754114B2

Reaction notes

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