4-Nitrophenyl chloroformate → HCID 86730053, compound

HRID 1504593Notes

Reaction equation

HRID 1504593 reaction equation
[OH:1][CH:2]1[CH2:6][CH2:5][N:4]([C:7]2[CH:15]=[CH:14][C:10]([C:11]([NH2:13])=[O:12])=[CH:9][N:8]=2)[CH2:3]1.[C:16](Cl)(=[O:27])[O:17][C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=1>C(Cl)Cl>[C:16](=[O:27])([O:17][C:18]1[CH:19]=[CH:20][C:21]([N+:24]([O-:26])=[O:25])=[CH:22][CH:23]=1)[O:1][CH:2]1[CH2:6][CH2:5][N:4]([C:7]2[CH:15]=[CH:14][C:10]([C:11](=[O:12])[NH2:13])=[CH:9][N:8]=2)[CH2:3]1

Participants

4

Reactant 2

HCID 821294-Nitrophenyl chloroformateHCID 80345918HCID 80345918, compound

Product 1

HCID 86730053HCID 86730053, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-(3-hydroxypyrrolidin-1-yl)nicotinamide (0.27 g, 1 mmol) in DCM (5 ml) 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 (0.11 g, 30%) as a yellow liquid. [LCMS RtA=1.71 min, [M+H]+=373.1].

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-567e4dba09544911b2ba4536f0f79ef2
Source dataset
uspto-grants-2015_12
Patent number
US09216182B2

Reaction notes

Loading…