Isopropanol → HCID 178518479, compound

HRID 2036934Notes

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. To the reaction mixture, isopropanol (3 mL) was added in the along with 218 mg thiazolidine-2,4-dione and 94 μL of piperidine. The temperature was increased to 90° C. and the reaction was stirred at that temperature overnight. The precipitate was filtered while hot and dissolved in MeOH. To the reaction mixture, 1M HCl (1 mL) was added and the mixture sonicated. The precipitate was filtered and washed with MeOH 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

temperatureThe temperature was increased to 90° C.
filtrationThe precipitate was filtered while hot and
dissolutiondissolved in MeOH
additionTo the reaction mixture, 1M HCl (1 mL) was added
customthe mixture sonicated
filtrationThe precipitate was filtered
washwashed with MeOH

Sources & evidence

ORD record: ord-9bbb093234f14ac6a5baf67e58c667a0
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08575177B2

Reaction notes

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