HCID 178452355, compound → HCID 178518509, compound

HRID 624741Notes

Reaction equation

HRID 624741 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[CH:14]=[C:13]([NH:15][C:16]3[CH:17]=[C:18]([CH:34]=[CH:35][CH:36]=3)[C:19]([N:21]3[CH2:26][CH2:25][N:24](C(OC(C)(C)C)=O)[CH2:23][CH2:22]3)=[O:20])[N:12]3[N:37]=[CH:38][C:39]([CH:40]=[C:41]4[C:45](=[O:46])[NH:44][C:43](=[O:47])[NH:42]4)=[C:11]3[N:10]=2)[CH:5]=[CH:6][CH:7]=1>C(O)(C(F)(F)F)=O.C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[CH:14]=[C:13]([NH:15][C:16]3[CH:36]=[CH:35][CH:34]=[C:18]([C:19]([N:21]4[CH2:22][CH2:23][NH:24][CH2:25][CH2:26]4)=[O:20])[CH:17]=3)[N:12]3[N:37]=[CH:38][C:39]([CH:40]=[C:41]4[NH:42][C:43](=[O:47])[NH:44][C:45]4=[O:46])=[C:11]3[N:10]=2)[CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 178452355HCID 178452355, compound

Product 1

HCID 178518509HCID 178518509, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

Tert-butyl 4-(3-(5-(3-chlorophenylamino)-3-((2,5-dioxoimidazolidin-4-ylidene)methyl)pyrazolo[1,5-a]pyrimidin-7-ylamino)benzoyl)piperazine-1-carboxylate (27 mg, 0.04 mmol) was dissolved in 2 mL of TFA/DCM (1:1) and stirred at room temperature for 1 hour. Excess solvent and TFA were removed by evaporation under a stream of nitrogen. The residue was diluted with water then the mixture was filtered. The recovered solid was washed with water followed by 50% ethanol. The product, 5-((5-(3-chlorophenylamino)-7-(3-(piperazine-1-carbonyl)phenylamino)pyrazolo[1,5-a]pyrimidin-3-yl)methylene)imidazolidine-2,4-dione, was collected as a solid in 21% yield. LCMS (M+1=558)

Workup

  1. customExcess solvent and TFA were removed by evaporation under a stream of nitrogen
  2. additionThe residue was diluted with water
  3. filtrationthe mixture was filtered
  4. washThe recovered solid was washed with water
  5. customThe product, 5-((5-(3-chlorophenylamino)-7-(3-(piperazine-1-carbonyl)phenylamino)pyrazolo[1,5-a]pyrimidin-3-yl)methylene)imidazolidine-2,4-dione, was collected as a solid in 21% yield

Sources & evidence

ORD record
ord-d7d6139976b54f608f45b3f628abe497
Source dataset
uspto-grants-2016_04
Patent number
US09303033B2

Reaction notes

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