Acetonitrile → HCID 73053630, compound

HRID 870456Notes

Reaction equation

HRID 870456 reaction equation
[Cl:1][C:2]1[CH:17]=[C:16]([NH:18][C:19]([C:21]2[C:22](=[O:34])[N:23]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[N:24]([CH3:27])[C:25]=2[CH3:26])=[O:20])[CH:15]=[CH:14][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7](C(N)=O)[CH:6]=1.C(O)(=O)C.C(O)(=O)C.IC1C=CC=CC=1.CC#[N:52]>CCOC(C)=O.O>[NH2:52][C:7]1[CH:6]=[C:5]([O:4][C:3]2[CH:14]=[CH:15][C:16]([NH:18][C:19]([C:21]3[C:22](=[O:34])[N:23]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[N:24]([CH3:27])[C:25]=3[CH3:26])=[O:20])=[CH:17][C:2]=2[Cl:1])[CH:10]=[CH:9][N:8]=1

Participants

6

Reactant 3

HCID 6342AcetonitrileHCID 12217721Iodo benzene diacetateHCID 73050921HCID 73050921, compound

Product 1

HCID 73053630HCID 73053630, compoundYield 52.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of 4-(2-chloro-4-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamido)phenoxy)picolinamide (540 mg, 1.13 mmol) in EtOAc (6 mL), CH3CN (6 mL) and H2O (3 mL) was added iodobenzene diacetate (438 mg, 1.36 mmol) at 0° C. The mixture was stirred at 0° C. for 30 minutes, then warmed up to rt and stirred for 4.5 hours. The mixture was concentrated in vacuo and the residue was purified by a silica gel column chromatography (EtOAc/PE (v/v)=6/1) to give the title compound as a beige solid (265 mg, 52.2%).

Workup

  1. temperaturewarmed up to rt
  2. stirringstirred for 4.5 hours
  3. concentrationThe mixture was concentrated in vacuo
  4. customthe residue was purified by a silica gel column chromatography (EtOAc/PE (v/v)=6/1)

Sources & evidence

ORD record
ord-961cc8864ef94866b746a557902088a0
Source dataset
uspto-grants-2015_03
Patent number
US08969388B1

Reaction notes

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