Ethanolamine → 5-[[5-(3-chloroanilino)-7-(2-hydroxyethylamino)pyrazolo[1,5-a]pyrimidin-3-yl]methylidene]imidazolidine-2,4-dione

HRID 624734Notes

Reaction equation

C(S([C:10]1[N:15]2[N:16]=[CH:17][C:18]([CH:19]=[C:20]3[NH:24][C:23](=[O:25])[NH:22][C:21]3=[O:26])=[C:14]2[N:13]=[C:12]([NH:27][C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([Cl:34])[CH:29]=2)[CH:11]=1)=O)C1C=CC=CC=1.[NH2:35][CH2:36][CH2:37][OH:38].O>CN1C(=O)CCC1>[Cl:34][C:30]1[CH:29]=[C:28]([NH:27][C:12]2[CH:11]=[C:10]([NH:35][CH2:36][CH2:37][OH:38])[N:15]3[N:16]=[CH:17][C:18]([CH:19]=[C:20]4[NH:24][C:23](=[O:25])[NH:22][C:21]4=[O:26])=[C:14]3[N:13]=2)[CH:33]=[CH:32][CH:31]=1

Participants

Conditions

Temperature: 120 °C

Procedure

To 5-((7-(benzylsulfinyl)-5-(3-chlorophenylamino)pyrazolo[1,5-a]pyrimidin-3-yl)methylene)imidazolidine-2,4-dione (15 mg, 0.0304 mmol) in NMP was added 2-aminoethanol (14.6 μL, 0.242 mmol). The mixture was heated in the microwave at 120° C. for 20 minutes. Water was added to the reaction mixture and the precipitate was collected by filtration. The precipitate was washed with methanol to yield 5-((5-(3-chlorophenylamino)-7-(2-hydroxyethylamino)pyrazolo[1,5-a]pyrimidin-3-yl)methylene)imidazolidine-2,4-dione LCMS (M+1=414). Similar products (shown below) were also obtained as precipitates by addition of water while other reactions were purified by prep HPLC to yield corresponding products.

Workup

filtrationthe precipitate was collected by filtration
washThe precipitate was washed with methanol

Sources & evidence

ORD record: ord-851085d437ad417d886b047e35b3f62c
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09303033B2

Reaction notes

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