5-[[5-benzylsulfanyl-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidin-3-yl]methylidene]imidazolidine-2,4-dione → HCID 178518497, compound

HRID 624707Notes

Reaction equation

HRID 624707 reaction equation
[CH2:1]([S:8][C:9]1[CH:14]=[C:13]([NH:15][CH:16]2[CH2:18][CH2:17]2)[N:12]2[N:19]=[CH:20][C:21]([CH:22]=[C:23]3[NH:27][C:26](=[O:28])[NH:25][C:24]3=[O:29])=[C:11]2[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>ClCCl.FC(F)(F)C(O)=O>[CH2:1]([S:8][C:9]1[CH:14]=[C:13]([NH:15][CH:16]2[CH2:18][CH2:17]2)[N:12]2[N:19]=[CH:20][C:21](/[CH:22]=[C:23]3/[C:24](=[O:29])[NH:25][C:26](=[O:28])[NH:27]/3)=[C:11]2[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 1785184985-[[5-benzylsulfanyl-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidin-3-yl]methylidene]imidazolidine-2,4-dione

Product 1

HCID 178518497HCID 178518497, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

5-((5-(Benzylthio)-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidin-3-yl)methylene)imidazolidine-2,4-dione (60 mg, 0.15 mmol) was dissolved in dichloromethane (1 mL) and trifluoroacetic acid (1 mL). After 1 h, the solution was concentrated under a stream of air. The residue was triturated with Et2O (3 mL) and the precipitate was collected to provide (Z)-5-((5-(benzylthio)-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidin-3-yl)methylene)imidazolidine-2,4-dione (59 mg, 98%). LCMS (ES): >95% pure, m/z 407 [M+1]+.

Workup

  1. concentrationthe solution was concentrated under a stream of air
  2. customThe residue was triturated with Et2O (3 mL)
  3. customthe precipitate was collected

Sources & evidence

ORD record
ord-cab6420927ca4d60b71f9bb521319a4c
Source dataset
uspto-grants-2016_04
Patent number
US09303033B2

Reaction notes

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