Sodium Hydroxide → 3-[3-[[2-[3-(2,2-Dimethylpropanoylamino)-4-methyl-phenyl]imidazo[2,1-f]pyridazin-6-yl]carbamoyl]phenyl]prop-2-enoic acid

HRID 539805Notes

Reaction equation

C([O:3][C:4](=[O:39])[CH:5]=[CH:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13](=[O:38])[NH:14][C:15]2[CH:20]=[CH:19][C:18]3=[N:21][C:22]([C:24]4[CH:29]=[CH:28][C:27]([CH3:30])=[C:26]([NH:31][C:32](=[O:37])[C:33]([CH3:36])([CH3:35])[CH3:34])[CH:25]=4)=[CH:23][N:17]3[N:16]=2)[CH:8]=1)C.[OH-].[Na+]>C1COCC1.CO>[CH3:34][C:33]([CH3:36])([CH3:35])[C:32]([NH:31][C:26]1[CH:25]=[C:24]([C:22]2[N:21]=[C:18]3[N:17]([CH:23]=2)[N:16]=[C:15]([NH:14][C:13]([C:9]2[CH:8]=[C:7]([CH:6]=[CH:5][C:4]([OH:39])=[O:3])[CH:12]=[CH:11][CH:10]=2)=[O:38])[CH:20]=[CH:19]3)[CH:29]=[CH:28][C:27]=1[CH3:30])=[O:37]

Participants

Conditions

Temperature: 50 °C

Procedure

A 20-mL vial is charged with ethyl-3-[3-[[2-[3-(2,2-dimethylpropanoylamino)-4-methyl-phenyl]imidazo[2,1-f]pyridazin-6-yl]carbamoyl]phenyl]prop-2-enoate (0.042 g, 0.08 mmol) and a solution of THF-MeOH (1 mL, 1:1). To this mixture is added aqueous NaOH (1 mL, 1 M), then stirred at 50° C. for 1 hour. The mixture is concentrated to remove the organics and extracted with EtOAc once. Aqueous HCl (1M) is added to lower the pH to 2 and the resulting solids are filtered to give the title compound (0.025 g), which is used without further purification. LCMS (m/z)=498.5 [M+H]+, tR=2.47 min.

Workup

concentrationThe mixture is concentrated
customto remove the organics and
extractionextracted with EtOAc once
additionAqueous HCl (1M) is added
filtrationthe resulting solids are filtered

Sources & evidence

ORD record: ord-d010a2e2766649c184dce2e6e7f1dfb5
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871767B2

Reaction notes

Loading…