Triethylamine → HCID 69225680, compound

HRID 1027875Notes

Reaction equation

HRID 1027875 reaction equation
Cl[C:2]1[C:7]2[CH2:8][CH2:9][O:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[C:6]=2[N:5]=[C:4]([NH2:17])[N:3]=1.C(N(CC)CC)C.[C:25]([O:29][C:30]([N:32]1[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]1)=[O:31])([CH3:28])([CH3:27])[CH3:26]>C(O)C.C(Cl)Cl>[C:25]([O:29][C:30]([N:32]1[CH2:37][CH2:36][N:35]([C:2]2[C:7]3[CH2:8][CH2:9][O:10][C:11]4[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=4[C:6]=3[N:5]=[C:4]([NH2:17])[N:3]=2)[CH2:34][CH2:33]1)=[O:31])([CH3:28])([CH3:26])[CH3:27]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 87741012HCID 87741012, compound

Product 1

HCID 69225680HCID 69225680, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of Example 29D (29 mg, 0.12 mmol) in ethanol (0.5 mL) was added triethylamine (0.12 mL, 0.82 mmol), piperazine-1-carboxylic acid tert-butyl ester (33 mg, 0.18 mmol) and the mixture heated at 90° C. for 16 hours. The mixture was diluted with CH2Cl2 (25 mL) and washed with 1 M NaOH (10 mL). The layers were separated and the aqueous was extracted with CH2Cl2 (25 mL). The combined CH2Cl2 layers were dried (MgSO4), filtered, concentrated under reduced pressure and chromatographed on silica gel eluting with a gradient of CH2Cl2:EtOAc (5:1, 2:1 and 1:1) to provide the title compound. 1H NMR (CDCl3) δ 1.49 (s, 9H), 2.72 (t, J=5.93 Hz, 2H), 3.26-3.32 (m, 4H), 3.52-3.57 (m, 4H), 4.54 (t, J=5.93 Hz, 2H), 4.78 (s, 2H), 7.09 (dd, J=8.14, 1.36 Hz, 1H), 7.17-7.24 (m, 1H), 7.35-7.42 (m, 1H), 7.89 (dd, J=7.80, 1.70 Hz, 1H).

Workup

  1. washwashed with 1 M NaOH (10 mL)
  2. customThe layers were separated
  3. extractionthe aqueous was extracted with CH2Cl2 (25 mL)
  4. dry with materialThe combined CH2Cl2 layers were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customchromatographed on silica gel eluting with a gradient of CH2Cl2:EtOAc (5:1, 2:1 and 1:1)

Sources & evidence

ORD record
ord-20c6c02d745a4aa2bb2baabeaea4ed48
Source dataset
uspto-grants-2014_05
Patent number
US08735411B2

Reaction notes

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