HCID 178418806, compound → 3-[[[5-[[4-[3-(dimethylamino)propoxy]phenyl]methyl]-1H-pyrazol-3-yl]amino]methylidene]-1H-indol-2-one

HRID 746729Notes

Reaction equation

HRID 746729 reaction equation
NC1C=CNN=1.O/[CH:8]=[C:9]1\[C:10](=[O:18])[NH:11][C:12]2[C:17]\1=[CH:16][CH:15]=[CH:14][CH:13]=2.[CH3:19][N:20]([CH3:38])[CH2:21][CH2:22][CH2:23][O:24][C:25]1[CH:37]=[CH:36][C:28]([CH2:29][C:30]2[CH:31]=[C:32]([NH2:35])[NH:33][N:34]=2)=[CH:27][CH:26]=1>O1CCCC1>[CH3:38][N:20]([CH3:19])[CH2:21][CH2:22][CH2:23][O:24][C:25]1[CH:37]=[CH:36][C:28]([CH2:29][C:30]2[CH:31]=[C:32]([NH:35][CH:8]=[C:9]3[C:17]4[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=4)[NH:11][C:10]3=[O:18])[NH:33][N:34]=2)=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 178418806HCID 178418806, compoundHCID 178483571HCID 178483571, compoundHCID 178517101HCID 178517101, compound

Product 1

HCID 1784835703-[[[5-[[4-[3-(dimethylamino)propoxy]phenyl]methyl]-1H-pyrazol-3-yl]amino]methylidene]-1H-indol-2-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The named compound is prepared by substituting 5-[4-(3-dimethylamino-propoxy)-benzyl]-2H-pyrazol-3-ylamine for 3-aminopyrazole in the reaction of Example 1. Specifically, E & Z-3-[(hydroxy)-methylene]-1,3-dihydro-indol-2-one (0.0351 gms.) is reacted with 0.0881 gms. of 5-[4-(3-dimethylamino-propoxy)-benzyl]-2H-pyrazol-3-ylamine by refluxing in tetrahydrofuran (2.0 mL). Recrystallization from a mixture of ethyl acetate and hexanes affords the named compound.

Workup

  1. customThe named compound is prepared
  2. customin the reaction of Example 1
  3. customRecrystallization
  4. additionfrom a mixture of ethyl acetate and hexanes
  5. customaffords the named compound

Sources & evidence

ORD record
ord-3973bff4d56c432db1bca8f188905aee
Source dataset
uspto-grants-2008_07
Patent number
US07393870B2

Reaction notes

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