Reaction #1583826

ord-d2c6227684bf4edea1dc63c49057823b

Reaction equation

COC(=O)NCc1cc(C(=O)C=CN(C)C)ccc1Cl
methyl N-[[2-chloro-5-[3-(dimethylamino)-1-oxo-2-propen-1-yl]phenyl]methyl]carbamate
COC(=O)NCc1cc(C(=O)C=CN(C)C)ccc1Cl
product
COC(=O)NCc1cc(C(=O)C=CN(C)C)ccc1Cl
methyl N-[[2-chloro-5-[3-(dimethylamino)-1-oxo-2-propen-1-yl]phenyl]methyl]carbamate
NN.O
hydrazine hydrate
COC(=O)NCc1cc(-c2cc[nH]n2)ccc1Cl
title compound
COC(=O)NCc1cc(-c2cc[nH]n2)ccc1Cl
methyl N-[[2-chloro-5-(1H-pyrazol-3-yl)phenyl]methyl]carbamate

Solvents

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    FiltrationThe reaction mixture was filtered
  2. 2
    Otherthe solid collected
  3. 3
    Otherwas dried under reduced pressure

Procedure

To a solution of methyl N-[[2-chloro-5-[3-(dimethylamino)-1-oxo-2-propen-1-yl]phenyl]methyl]carbamate (i.e. the product of Step A) (4.14 g, 13.9 mmol) in methanol (80 mL) was added hydrazine hydrate (0.771 g, 15.4 mmol). The reaction mixture was stirred at room temperature for 2 days. The reaction mixture was filtered and the solid collected was dried under reduced pressure to provide the title compound, a compound of the present invention, as a solid (3.26 g).

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US09198433B2uspto-grants-2015_12