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 411727Notes

Reaction equation

HRID 411727 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-0c991ed2e32842c5a7d6f14320e7a30a
Source dataset
uspto-grants-2003_05
Patent number
US06559173B1

Reaction notes

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