HCID 178452080, compound → HCID 178518511, compound

HRID 624722Notes

Reaction equation

HRID 624722 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[CH:14]=[C:13]([NH:15][CH:16]3[CH2:21][CH2:20][N:19](C(OC(C)(C)C)=O)[CH2:18][CH2:17]3)[N:12]3[N:29]=[CH:30][C:31]([CH:32]=[C:33]4[C:37](=[O:38])[NH:36][C:35](=[O:39])[NH:34]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][CH:16]3[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]3)[N:12]3[N:29]=[CH:30][C:31]([CH:32]=[C:33]4[NH:34][C:35](=[O:39])[NH:36][C:37]4=[O:38])=[C:11]3[N:10]=2)[CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 178452080HCID 178452080, compound

Product 1

HCID 178518511HCID 178518511, compound

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

Tert-butyl 4-(5-(3-chlorophenylamino)-3-((2,5-dioxoimidazolidin-4-ylidene)methyl)pyrazolo[1,5-a]pyrimidin-7-ylamino)piperidine-1-carboxylate (640 mg, 1.2 mmol) was dissolved in 10 mL of TFA/DCM (1:1) and stirred at room temperature for 1 hour then quenched by addition to ice cold 6N NaOH. The mixture was diluted with water then the aqueous layer was decanted. The organic layer was diluted with hexanes and filtered. The product, 5-((5-(3-chlorophenylamino)-7-(piperidin-4-ylamino)pyrazolo[1,5-a]pyrimidin-3-yl)methylene)imidazolidine-2,4-dione, was collected as a solid in quantitative yield. LCMS (M+1=453)

Workup

  1. customthen quenched by addition to ice cold 6N NaOH
  2. additionThe mixture was diluted with water
  3. customthe aqueous layer was decanted
  4. additionThe organic layer was diluted with hexanes
  5. filtrationfiltered
  6. customThe product, 5-((5-(3-chlorophenylamino)-7-(piperidin-4-ylamino)pyrazolo[1,5-a]pyrimidin-3-yl)methylene)imidazolidine-2,4-dione, was collected as a solid in quantitative yield

Sources & evidence

ORD record
ord-f41d110ec9b7499986d2b29229005436
Source dataset
uspto-grants-2016_04
Patent number
US09303033B2

Reaction notes

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