Diisopropylethylamine → HCID 89077758, compound

HRID 1397043Notes

Reaction equation

Cl.[O:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[C:7]([N:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1)=[NH:8].CS([C:19]1[N:24]=[C:23](/[CH:25]=[C:26]2/[C:27](=[O:32])[NH:28][C:29](=[O:31])[S:30]/2)[CH:22]=[CH:21][N:20]=1)(=O)=O.C(N(C(C)C)C(C)C)C>CS(C)=O>[O:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[C:7](=[NH:8])[N:9]1[CH2:10][CH2:11][N:12]([C:19]2[N:24]=[C:23](/[CH:25]=[C:26]3/[C:27](=[O:32])[NH:28][C:29](=[O:31])[S:30]/3)[CH:22]=[CH:21][N:20]=2)[CH2:13][CH2:14]1

Participants

Conditions

Temperature: 100 °C

Procedure

The crude material from Step 2, furan-2-yl(piperazin-1-yl)methanimine hydrochloride (16.3 mg, 0.076 mmol) was diluted in DMSO (Volume: 0.75 mL) and added to (Z)-5-((2-(methylsulfonyl)pyrimidin-4-yl)methylene)thiazolidine-2,4-dione (19.4 mg, 0.068 mmol) in a 2-dram vial. The reaction solution was then treated with N-ethyl-N-isopropylpropan-2-amine (50 mg, 0.387 mmol) and then shaken at 100° C. for 16 h. The reaction was then purified by RP-HPLC using TFA as the modifier to provide (Z)-5-((2-(4-(furan-2-yl(imino)methyl)piperazin-1-yl)pyrimidin-4-yl)methylene)thiazolidine-2,4-dione.

Workup

customThe reaction was then purified by RP-HPLC

Sources & evidence

ORD record: ord-e03993f2891d489aad4e9ba6a5e3744b
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08901145B2

Reaction notes

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