3-(furan-2-yl)-1H-pyrazol-5-amine → 6-fluoro-3-[[[5-(furan-2-yl)-1H-pyrazol-3-yl]amino]methylidene]-1H-indol-2-one

HRID 892079Notes

Reaction equation

HRID 892079 reaction equation
O/[CH:2]=[C:3]1\[C:4](=[O:13])[NH:5][C:6]2[C:11]\1=[CH:10][CH:9]=[C:8]([F:12])[CH:7]=2.O/C=C1\C(=O)NC2C\1=CC=CC=2.[O:26]1[CH:30]=[CH:29][CH:28]=[C:27]1[C:31]1[NH:35][N:34]=[C:33]([NH2:36])[CH:32]=1.NC1C=CNN=1>O1CCCC1>[F:12][C:8]1[CH:7]=[C:6]2[C:11]([C:3](=[CH:2][NH:36][C:33]3[CH:32]=[C:31]([C:27]4[O:26][CH:30]=[CH:29][CH:28]=4)[NH:35][N:34]=3)[C:4](=[O:13])[NH:5]2)=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 5231833-(furan-2-yl)-1H-pyrazol-5-amine2×HCID 178418806HCID 178418806, compoundHCID 178517101HCID 178517101, compoundHCID 178517312(3Z)-6-fluoro-3-(hydroxymethylidene)-1H-indol-2-one2×

Product 1

HCID 1785173116-fluoro-3-[[[5-(furan-2-yl)-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]-6-fluoro-1,3-dihydro-indol-2-one for E & Z-3-[(hydroxy)-methylene]-1,3-dihydro-indol-2-one and 5-furan-2-yl-1H-pyrazol-3-ylamine for 3-aminopyrazole in the reaction of Example 1. Specifically, E & Z-3-[(hydroxy)-methylene]-6-fluoro-1,3-dihydro-indol-2-one (0.033 gms.) is reacted with 0.061 gms. 5-furan-2-yl-1H-pyrazol-3-ylamine by refluxing in tetrahydrofuran (0.88 mL) to afford the named compound in the amount of 0.0263 gms.

Workup

  1. customThe named compound is prepared
  2. customin the reaction of Example 1
  3. customto afford the named compound in the amount of 0.0263 gms

Sources & evidence

ORD record
ord-1beb1831c272445aa1ff46281e283319
Source dataset
uspto-grants-2006_02
Patent number
US07005444B2

Reaction notes

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