4-Nitrophenyl chloroformate → HCID 86730055, compound

HRID 1504596Notes

Reaction equation

HRID 1504596 reaction equation
[OH:1][CH:2]1[CH2:5][N:4]([C:6]2[CH:14]=[CH:13][C:9]([C:10]([NH2:12])=[O:11])=[CH:8][N:7]=2)[CH2:3]1.[C:15](Cl)(=[O:26])[O:16][C:17]1[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=1>C(Cl)Cl>[C:15](=[O:26])([O:16][C:17]1[CH:18]=[CH:19][C:20]([N+:23]([O-:25])=[O:24])=[CH:21][CH:22]=1)[O:1][CH:2]1[CH2:5][N:4]([C:6]2[CH:14]=[CH:13][C:9]([C:10](=[O:11])[NH2:12])=[CH:8][N:7]=2)[CH2:3]1

Participants

4

Reactant 2

HCID 821294-Nitrophenyl chloroformateHCID 78992995HCID 78992995, compound

Product 1

HCID 86730055HCID 86730055, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-(3-hydroxyazetidin-1-yl)nicotinamide (0.19 g, 1 mmol) in DCM (5 mL) under nitrogen was added 4-nitrophenyl carbonochloridate (0.20 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 title compound (36 mg, 10%) as a yellow liquid. [LCMS RtA=1.71 min, [M+H]+=359.0].

Workup

  1. filtrationThe reaction mixture was then filtered
  2. washthe filter cake was washed with DCM
  3. concentrationThe combined filtrates were concentrated

Sources & evidence

ORD record
ord-df339d41ae98444dae31b6274123f3ed
Source dataset
uspto-grants-2015_12
Patent number
US09216182B2

Reaction notes

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