3-Amino-5-phenylpyrazole → 5-chloro-3-[[(5-phenyl-1H-pyrazol-3-yl)amino]methylidene]-1H-indol-2-one

HRID 411677Notes

Reaction equation

HRID 411677 reaction equation
O/[CH:2]=[C:3]1\[C:4](=[O:13])[NH:5][C:6]2[C:11]\1=[CH:10][C:9]([Cl:12])=[CH:8][CH:7]=2.O/C=C1\C(=O)NC2C\1=CC=CC=2.[NH2:26][C:27]1[CH:31]=[C:30]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[NH:29][N:28]=1.NC1C=CNN=1>O1CCCC1>[Cl:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[NH:5][C:4](=[O:13])[C:3]2=[CH:2][NH:26][C:27]1[CH:31]=[C:30]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[NH:29][N:28]=1

Participants

6

Reactant 4

HCID 1366553-Amino-5-phenylpyrazole2×HCID 178418806HCID 178418806, compoundHCID 178517101HCID 178517101, compoundHCID 178517165HCID 178517165, compound2×

Product 1

HCID 1785171615-chloro-3-[[(5-phenyl-1H-pyrazol-3-yl)amino]methylidene]-1H-indol-2-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The named compound is prepared by substituting E & Z-3-[(hydroxy)-methylene]-5-chloro-1,3-dihydro-indol-2-one for E & Z-3-[(hydroxy)-methylene]-1,3-dihydro-indol-2-one and 3-amino-5-phenylpyrazole for 3-aminopyrazole in the reaction of Example 1. Specifically, E & Z-3-[(hydroxy)-methylene]-5-chloro-1,3-dihydro-indol-2-one (0.100 gms.) is reacted with 0.1668 gms. of 3-amino-5-phenylpyrazole by refluxing in tetrahydrofuran (2.5 mL).

Workup

  1. customThe named compound is prepared
  2. customin the reaction of Example 1

Sources & evidence

ORD record
ord-846cfefd044c4610a819238e262cbb8e
Source dataset
uspto-grants-2003_05
Patent number
US06559173B1

Reaction notes

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