1-Isopropylpiperazine → HCID 86730056, compound

HRID 1504597Notes

Reaction equation

HRID 1504597 reaction equation
[C:1](=[O:26])(OC1C=CC([N+]([O-])=O)=CC=1)[O:2][CH:3]1[CH2:6][N:5]([C:7]2[CH:12]=[CH:11][C:10]([C:13](=[O:15])[NH2:14])=[CH:9][N:8]=2)[CH2:4]1.[CH:27]([N:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1)([CH3:29])[CH3:28]>C(Cl)Cl>[CH:27]([N:30]1[CH2:35][CH2:34][N:33]([C:1]([O:2][CH:3]2[CH2:4][N:5]([C:7]3[CH:12]=[CH:11][C:10]([C:13](=[O:15])[NH2:14])=[CH:9][N:8]=3)[CH2:6]2)=[O:26])[CH2:32][CH2:31]1)([CH3:29])[CH3:28]

Participants

4

Reactant 2

HCID 780131-IsopropylpiperazineHCID 86730055HCID 86730055, compound

Product 1

HCID 86730056HCID 86730056, compoundYield 10.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(5-carbamoylpyridin-2-yl)-azetidin-3-yl 4-nitrophenyl carbonate (0.36 g, 1 mmol) in DCM (5 mL) under nitrogen 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 (35 mg, 10%) was obtained as a yellow solid. [1HNMR (500 MHz, CDCl3) δ8.58 (d, 1H), 7.96 (dd, 1H), 7.76 (s, 1H), 7.77 (s, 1H), 7.15 (s, 1H), 6.41 (d, 1H), 5.21 (m, 1H), 4.32 (m, 2H), 3.92 (m, 2H), 3.41 (m, 4H), 2.65 (m, 1H), 2.40 (m, 4H), 0.95 (d, 6H); LCMS RtA=1.59 min, [M+H]+=348.2].

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-c80b866830254c9d81ac25982a7f7ae2
Source dataset
uspto-grants-2015_12
Patent number
US09216182B2

Reaction notes

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