1,1'-Carbonyldiimidazole → N-(1-(4-cyanophenyl)-3,3-dimethyl-1-oxobutan-2-yl)-4-(6-methylpyridin-2-yl)piperazine-1-carboxamide

HRID 535779Notes

Reaction equation

HRID 535779 reaction equation
Cl.[NH2:2][CH:3]([C:14]([CH3:17])([CH3:16])[CH3:15])[C:4]([C:6]1[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[CH:8][CH:7]=1)=[O:5].C1N=CN([C:23](N2C=NC=C2)=[O:24])C=1.[CH3:30][C:31]1[N:36]=[C:35]([N:37]2[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]2)[CH:34]=[CH:33][CH:32]=1>CC#N>[C:10]([C:9]1[CH:12]=[CH:13][C:6]([C:4](=[O:5])[CH:3]([NH:2][C:23]([N:40]2[CH2:41][CH2:42][N:37]([C:35]3[CH:34]=[CH:33][CH:32]=[C:31]([CH3:30])[N:36]=3)[CH2:38][CH2:39]2)=[O:24])[C:14]([CH3:17])([CH3:16])[CH3:15])=[CH:7][CH:8]=1)#[N:11]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 27369461-(6-Methylpyridin-2-yl)piperazineHCID 682779744-(2-Amino-3,3-dimethylbutanoyl)benzonitrile hydrochloride

Product 1

HCID 56961883N-(1-(4-cyanophenyl)-3,3-dimethyl-1-oxobutan-2-yl)-4-(6-methylpyridin-2-yl)piperazine-1-carboxamideYield 37.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-(2-Amino-3,3-dimethylbutanoyl)benzonitrile hydrochloride (Example 3, 50 mg, 0.23 mmol) was added to a solution of CDI (112 mg, 0.69 mmol) and TEA (0.035 mL, 0.25 mmol) in MeCN (5 mL). The reaction mixture was stirred at rt for 90 minutes before 1-(6-methylpyridin-2-yl)piperazine (CAS 55745-89-6, 205 mg, 1.16 mmol) was added. The mixture was stirred for 1 h and the solvent was evaporated under reduced pressure. The product was dissolved in methanol, filtered and purified by prep. HPLC yielding N-(1-(4-cyanophenyl)-3,3-dimethyl-1-oxobutan-2-yl)-4-(6-methylpyridin-2-yl)piperazine-1-carboxamide (36.3 mg, 37%).

Workup

  1. additionwas added
  2. customthe solvent was evaporated under reduced pressure
  3. dissolutionThe product was dissolved in methanol
  4. filtrationfiltered
  5. custompurified by prep

Sources & evidence

ORD record
ord-dd590cdc668e4a9d9ab05f80eed7ff09
Source dataset
uspto-grants-2014_10
Patent number
US08859556B2

Reaction notes

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