Hydrochloric Acid → HCID 58285162, compound

HRID 1961518Notes

Reaction equation

HRID 1961518 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]2[C:16]([C:17]#[N:18])=[CH:15][NH:14][N:13]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].[Cl:19][C:20]1[CH:25]=[CH:24][C:23](B(O)O)=[CH:22][CH:21]=1.N1C=CC=CC=1.Cl>C(Cl)Cl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([N:14]2[CH:15]=[C:16]([C:17]#[N:18])[C:12]([NH:11][C:8]3[CH:7]=[CH:6][C:5]([S:2]([CH3:1])(=[O:3])=[O:4])=[CH:10][CH:9]=3)=[N:13]2)=[CH:22][CH:21]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 742994-Chlorophenylboronic acidHCID 178504790HCID 178504790, compound

Product 1

HCID 58285162HCID 58285162, compound

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

3-{[4-(methylsulfonyl)phenyl]amino}-1H-pyrazole-4-carbonitrile (64 mg, 0.244 mmol), copper(II) acetate (66.5 mg, 0.366 mmol), (4-chlorophenyl)boronic acid (76 mg, 0.488 mmol) and pyridine (0.079 mL, 0.976 mmol) were stirred in DCM (8 mL) at room temperature overnight. 2 N HCl was added and the products extracted into EtOAc (×2). The combined organic extracts were washed with brine, dried over MgSO4 and concentrated in vacuo. Purification of the residue twice by MPLC (5-60% EtOAc-hexanes) gave 1-(4-chlorophenyl)-3-{[4-(methylsulfonyl)phenyl]amino}-1H-pyrazole-4-carbonitrile as a white solid. 1-(4-chlorophenyl)-5-{[4-(methylsulfonyl)phenyl]amino}-1H-pyrazole-4-carbonitrile was also isolated.

Workup

  1. extractionthe products extracted into EtOAc (×2)
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customPurification of the residue twice by MPLC (5-60% EtOAc-hexanes)

Sources & evidence

ORD record
ord-d2f994aee4f446008de3506dd0a3662d
Source dataset
uspto-grants-2013_04
Patent number
US08415346B2

Reaction notes

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