Isopropanol → HCID 178518479, compound

HRID 624777Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][CH:9]2[CH2:11][CH2:10]2)[N:5]2[N:12]=[CH:13][C:14]([CH:15]=O)=[C:4]2[N:3]=1.[S:17]1[CH2:21][C:20](=[O:22])[NH:19][C:18]1=[O:23].N1CCCCC1.C(O)(C)C>CCO>[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][CH:9]2[CH2:10][CH2:11]2)[N:5]2[N:12]=[CH:13][C:14]([CH:15]=[C:21]3[S:17][C:18](=[O:23])[NH:19][C:20]3=[O:22])=[C:4]2[N:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To 5-chloro-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidine-3-carbaldehyde (440 mg, 1.86 mmol) in EtOH was added thiazolidine-2,4-dione (458 mg, 3.91 mmol) and piperidine (208 μl, 2.05 mmol). The reaction was heated at 80° C. overnight. 3 mL Isopropanol was added in the morning, along with 218 mg thiazolidine-2,4-dione, 94 μL piperidine. Temperature was increased to 90° C. and left overnight. Precipitate was filtered while hot and dissolved in methanol. 1 mL of 1M HCl was added and the mixture sonicated. Precipitate was filtered and washed with methanol to yield 340 mg (54% yield) 5-((5-chloro-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidin-3-yl)methylene)thiazolidine-2,4-dione as a yellow powder. LCMS (M+1=336)

Workup

temperatureTemperature was increased to 90° C.
filtrationPrecipitate was filtered while hot and
dissolutiondissolved in methanol
addition1 mL of 1M HCl was added
customthe mixture sonicated
filtrationPrecipitate was filtered
washwashed with methanol

Sources & evidence

ORD record: ord-6b311377fcc247edb447f2550f98fa54
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09303033B2

Reaction notes

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