Dimethylformamide dimethyl acetal → HCID 57929968, compound

HRID 1930022Notes

Reaction equation

[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9](=[O:23])[CH2:10][C:11]1[CH:12]=[CH:13][C:14]2[N:15]([C:17]([CH:20]([CH3:22])[CH3:21])=[N:18][N:19]=2)[N:16]=1.CO[CH:26](OC)[N:27](C)C.C([O-])(=O)C.[K+].Cl.NO>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[O:23][N:27]=[CH:26][C:10]=1[C:11]1[CH:12]=[CH:13][C:14]2[N:15]([C:17]([CH:20]([CH3:21])[CH3:22])=[N:18][N:19]=2)[N:16]=1

Participants

Conditions

Temperature: 95 °C

Procedure

A solution of 1-(2,4-difluorophenyl)-2-(3-isopropyl-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)ethanone (0.10 g, 0.316 mmol; Preparation #K.1), N,N-dimethylformamide dimethyl acetal (0.070 g, 0.57 mmol) and toluene (2 mL) was heated at about 110° C. in an oil bath for about 30 min. The reaction mixture was cooled and then concentrated under reduced pressure. The residue was dissolved in EtOH (2.0 mL) and then potassium acetate (0.12 g, 1.26 mmol) and hydroxylamine hydrochloride (0.090 g, 1.26 mmol) were added. The mixture was heated at about 95° C. in an oil bath for about 30 min. The mixture was concentrated under reduced pressure and then acetic acid was added and the material was purified by RP-HPLC (Table 1, Method d). The appropriate fractions were lyophilized to give the title compound (0.063 g, 58%): LC/MS (Table 1, Method a) Rt=2.11 min; MS m/z: 342.2 (M+H)+.

Workup

temperatureThe reaction mixture was cooled
concentrationconcentrated under reduced pressure
dissolutionThe residue was dissolved in EtOH (2.0 mL)
concentrationThe mixture was concentrated under reduced pressure
additionacetic acid was added
customthe material was purified by RP-HPLC (Table 1, Method d)

Sources & evidence

ORD record: ord-cae4bfe09787405e929fd83b5b50a15d
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188083B2

Reaction notes

Loading…