1,2-Dichloroethane → HCID 178452355, compound

HRID 624740Notes

Reaction equation

HRID 624740 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:22]=[CH:23][CH:24]=3)[C:19](O)=[O:20])[N:12]3[N:25]=[CH:26][C:27]([CH:28]=[C:29]4[C:33](=[O:34])[NH:32][C:31](=[O:35])[NH:30]4)=[C:11]3[N:10]=2)[CH:5]=[CH:6][CH:7]=1.C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C.[N:53]1([C:59]([O:61][C:62]([CH3:65])([CH3:64])[CH3:63])=[O:60])[CH2:58][CH2:57][NH:56][CH2:55][CH2:54]1.C(Cl)CCl>O.CN(C=O)C>[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:22]=[CH:23][CH:24]=3)[C:19]([N:56]3[CH2:55][CH2:54][N:53]([C:59]([O:61][C:62]([CH3:65])([CH3:64])[CH3:63])=[O:60])[CH2:58][CH2:57]3)=[O:20])[N:12]3[N:25]=[CH:26][C:27]([CH:28]=[C:29]4[C:33](=[O:34])[NH:32][C:31](=[O:35])[NH:30]4)=[C:11]3[N:10]=2)[CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 143452tert-Butyl piperazine-1-carboxylateHCID 178518510HCID 178518510, compound

Product 1

HCID 178452355HCID 178452355, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To the reaction flask, 3-(5-(3-chlorophenylamino)-3-((2,5-dioxoimidazolidin-4-ylidene)methyl)pyrazolo[1,5-a]pyrimidin-7-ylamino)benzoic acid (30 mg, 0.06 mmol) was added to DMF (0.5 mL) along with HOBt (9.2 mg, 0.06 mmol), triethylamine (8.4 μL, 0.06 mmol) and tert-butyl piperazine-1-carboxylate (11.2 mg, 0.06 mmol). The reaction mixture was stirred at room temperature for 5 minutes then EDC (11.5 mg, 0.06 mmol) was added. The reaction was allowed to stir for an additional hour then diluted with water and filtered. The recovered solid was washed with more water followed by ethanol. The product, 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, was collected as a solid in 73% yield. LCMS (M+1=658)

Workup

  1. stirringto stir for an additional hour
  2. filtrationfiltered
  3. washThe recovered solid was washed with more water
  4. customThe product, 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, was collected as a solid in 73% yield

Sources & evidence

ORD record
ord-c72a65227a45468fb7ca9fda2a464760
Source dataset
uspto-grants-2016_04
Patent number
US09303033B2

Reaction notes

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