Thiazolidinedione → 5-((5-(4-Methyl-1,4-diazepan-1-yl)pyrazolo[1,5-a]pyrimidin-3-yl)methylene)thiazolidine-2,4-dione

HRID 383675Notes

Reaction equation

[CH3:1][N:2]1[CH2:8][CH2:7][CH2:6][N:5]([C:9]2[CH:14]=[CH:13][N:12]3[N:15]=[CH:16][C:17]([CH:18]=O)=[C:11]3[N:10]=2)[CH2:4][CH2:3]1.[S:20]1[CH2:24][C:23](=[O:25])[NH:22][C:21]1=[O:26].N1CCCCC1>CCO>[CH3:1][N:2]1[CH2:8][CH2:7][CH2:6][N:5]([C:9]2[CH:14]=[CH:13][N:12]3[N:15]=[CH:16][C:17]([CH:18]=[C:24]4[S:20][C:21](=[O:26])[NH:22][C:23]4=[O:25])=[C:11]3[N:10]=2)[CH2:4][CH2:3]1

Participants

Conditions

Temperature: 70 °C

Procedure

To 5-(4-methyl-1,4-diazepan-1-yl)pyrazolo[1,5-a]pyrimidine-3-carbaldehyde (36 mg, 0.138 mmol) in EtOH was added 2,4-thiazolidinedione (16 mg, 0.138 mmol) and piperidine (14 μL, 0.138 mmol). The mixture was heated at 70° C. and purified by HPLC to yield 5-((5-(4-methyl-1,4-diazepan-1-yl)pyrazolo[1,5-a]pyrimidin-3-yl)methylene)thiazolidine-2,4-dione. LCMS (M+1=359)

Workup

custompurified by HPLC

Sources & evidence

ORD record: ord-9f5289caca384c719fd2ed67facf6133
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08367681B2

Reaction notes

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