Toluene → HCID 136136829, compound

HRID 1930023Notes

Reaction equation

[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9](=O)[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[C:26](OC)([N:28](C)C)[CH3:27].C1(C)C=CC=CC=1.[NH2:40]N>O1CCOCC1>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:10]([C:11]2[CH:12]=[CH:13][C:14]3[N:15]([C:17]([CH:20]([CH3:22])[CH3:21])=[N:18][N:19]=3)[N:16]=2)=[C:26]([CH3:27])[NH:28][N:40]=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 (0.26 g, 0.82 mmol; Preparation #K.1), N,N-dimethylacetamide dimethyl acetal (0.22 g, 1.64 mmol) and toluene (5 mL) was heated at about 110° C. in an oil bath for about 45 min. The reaction mixture was cooled and then concentrated under reduced pressure. 1,4-Dioxane (5.0 mL) and hydrazine (0.055 g, 1.64 mmol) were added to the mixture and it was then heated at about 95° C. in an oil bath for about 1 h. 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 concentrated under reduced pressure to give a solid which was collected by filtration and dried to give the title compound (0.008 g, 3%): LC/MS (Table 1, Method a) Rt=1.99 min; MS m/z: 355.2 (M+H)+.

Workup

temperatureThe reaction mixture was cooled
concentrationconcentrated under reduced pressure
concentrationThe mixture was concentrated under reduced pressure
additionacetic acid was added
customthe material was purified by RP-HPLC (Table 1, Method d)
concentrationThe appropriate fractions were concentrated under reduced pressure
customto give a solid which
filtrationwas collected by filtration
customdried

Sources & evidence

ORD record: ord-611dbcfb34f3492b88e61780d58e032c
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188083B2

Reaction notes

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