1,2-Dichloroethane → HCID 178452355, compound

HRID 2036961Notes

Reaction equation

HRID 2036961 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-fb48512cdec74589a431f32cca7c66fb
Source dataset
uspto-grants-2013_11
Patent number
US08575177B2

Reaction notes

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