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

HRID 411731Notes

Reaction equation

HRID 411731 reaction equation
O/[CH:2]=[C:3]1\[C:4](=[O:13])[NH:5][C:6]2[C:11]\1=[C:10](C)[CH:9]=[CH:8][CH:7]=2.O/C=C1\C(=O)NC2C\1=CC=CC=2.[CH3:26][N:27]([CH3:45])[CH2:28][CH2:29][CH2:30][O:31][C:32]1[CH:44]=[CH:43][C:35]([CH2:36][C:37]2[CH:38]=[C:39]([NH2:42])[NH:40][N:41]=2)=[CH:34][CH:33]=1.NC1C=CNN=1>O1CCCC1>[CH3:45][N:27]([CH3:26])[CH2:28][CH2:29][CH2:30][O:31][C:32]1[CH:44]=[CH:43][C:35]([CH2:36][C:37]2[CH:38]=[C:39]([NH:42][CH:2]=[C:3]3[C:11]4[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=4)[NH:5][C:4]3=[O:13])[NH:40][N:41]=2)=[CH:34][CH:33]=1

Participants

6

Reactant 4

HCID 178418806HCID 178418806, compoundHCID 178423596HCID 178423596, compound2×HCID 178483571HCID 178483571, compound2×HCID 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 E & Z-3-[(hydroxy)-methylene]-4-methyl-1,3-dihydro-indol-2-one for E & Z-3-[(hydroxy)-methylene]-1,3-dihydro-indol-2-one and 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]-4-methyl-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-84b24370c42542fcabce28280575d0dc
Source dataset
uspto-grants-2003_05
Patent number
US06559173B1

Reaction notes

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