tert-Butyl piperazine-1-carboxylate → HCID 58168295, compound

HRID 1029142Notes

Reaction equation

HRID 1029142 reaction equation
Cl[C:2]1[CH:11]=[CH:10][N:9]=[C:8]2[C:3]=1[C:4]1[CH:16]=[CH:15][CH:14]=[CH:13][C:5]=1[C:6](=[O:12])[NH:7]2.[C:17]([N:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1)([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18].CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.CC([O-])(C)C.[Na+]>O1CCOCC1.CCOC(C)=O.O.CC([O-])=O.CC([O-])=O.[Pd+2]>[C:20]([O:19][C:17]([N:24]1[CH2:29][CH2:28][N:27]([C:2]2[CH:11]=[CH:10][N:9]=[C:8]3[C:3]=2[C:4]2[CH:16]=[CH:15][CH:14]=[CH:13][C:5]=2[C:6](=[O:12])[NH:7]3)[CH2:26][CH2:25]1)=[O:18])([CH3:23])([CH3:21])[CH3:22]

Participants

8

Reactant 4

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 23676156Sodium t-butoxideHCID 581680081-Chlorobenzo[C][1,8]naphthyridin-6(5H)-one

Product 1

HCID 58168295HCID 58168295, compoundYield 42.8%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 312751,4-DioxaneSolventHCID 22728543Water ethylacetateSolvent

Conditions

Temperature
100 °C

Procedure

Compound 83 (100 mg, 0.43 mmol), 1-Boc-piperazine (161 mg, 0.87 mmol), Pd(OAc)2 (5 mg, 0.02 mmol), X-Phos (21 mg, 0.04 mmol), and NaOtBu (167 mg, 1.73 mmol) were suspended in dioxane (2 mL), and stirred overnight at 100° C. The reaction mixture was diluted with EtOAc/H2O, and filtered through an Extrelut column. The column was washed with EtOAc, and the filtrate was concentrated. The crude product was purified via Biotage eluting with a gradient of 50 to 100% EtOAc in hexanes to provide 178 (70 mg, 42% yield) as a yellow solid. LC-MS (M+H=381, obsd.=381).

Workup

  1. filtrationfiltered through an Extrelut column
  2. washThe column was washed with EtOAc
  3. concentrationthe filtrate was concentrated
  4. customThe crude product was purified via Biotage
  5. washeluting with a gradient of 50 to 100% EtOAc in hexanes

Sources & evidence

ORD record
ord-bed473d110564ebc9da462d991d6c932
Source dataset
uspto-grants-2014_05
Patent number
US08735584B2

Reaction notes

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