1-Isopropylpiperazine → HCID 86730054, compound

HRID 1504594Notes

Reaction equation

HRID 1504594 reaction equation
[C:1](=[O:27])(OC1C=CC([N+]([O-])=O)=CC=1)[O:2][CH:3]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14](=[O:16])[NH2:15])=[CH:10][N:9]=2)[CH2:4]1.[CH:28]([N:31]1[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]1)([CH3:30])[CH3:29]>C(Cl)Cl>[CH:28]([N:31]1[CH2:36][CH2:35][N:34]([C:1]([O:2][CH:3]2[CH2:7][CH2:6][N:5]([C:8]3[CH:13]=[CH:12][C:11]([C:14](=[O:16])[NH2:15])=[CH:10][N:9]=3)[CH2:4]2)=[O:27])[CH2:33][CH2:32]1)([CH3:30])[CH3:29]

Participants

4

Reactant 2

HCID 780131-IsopropylpiperazineHCID 86730053HCID 86730053, compound

Product 1

HCID 86730054HCID 86730054, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(5-carbamoylpyridin-2-yl)-pyrrolidin-3-yl 4-nitrophenyl carbonate (0.37 g, 1 mmol) in DCM (5 ml) was added 1-isopropylpiperazine (0.13 g, 1 mmol). The resulting solution was stirred under N2 at room temperature for 24 h. The reaction mixture was then filtered and the filter cake was washed with DCM. The combined filtrates were concentrated to afford the crude product. After further purified by preparative HPLC, the title compound was obtained as a yellow solid (36 mg, 10%). [1H NMR (500 MHz, CDCl3) δ8.60 (d, 1H), 7.94 (dd, 1H), 7.72 (s, 1H), 7.09 (s, 1H), 6.48 (d, 1H), 5.25 (s, 1H), 3.66 (m, 2H), 3.55 (m, 2H), 3.31 (m, 4H), 2.63 (m, 1H), 2.36 (m, 4H), 2.21 (m, 1H), 2.10 (m, 1H), 0.92 (d, 6H, J=6.5 Hz); LCMS RtA=1.58 min, [M+H]+=362.2].

Workup

  1. filtrationThe reaction mixture was then filtered
  2. washthe filter cake was washed with DCM
  3. concentrationThe combined filtrates were concentrated
  4. customto afford the crude product
  5. customAfter further purified by preparative HPLC

Sources & evidence

ORD record
ord-e7767d0f36da47e4920a1f33de8860fc
Source dataset
uspto-grants-2015_12
Patent number
US09216182B2

Reaction notes

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