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

HRID 411734Notes

Reaction equation

HRID 411734 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.[N:19]1([CH2:25][CH2:26][CH2:27][O:28][C:29]2[CH:41]=[CH:40][C:32]([CH2:33][C:34]3[CH:35]=[C:36]([NH2:39])[NH:37][N:38]=3)=[CH:31][CH:30]=2)[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1>O1CCCC1>[N:19]1([CH2:25][CH2:26][CH2:27][O:28][C:29]2[CH:30]=[CH:31][C:32]([CH2:33][C:34]3[CH:35]=[C:36]([NH:39][CH:8]=[C:9]4[C:17]5[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=5)[NH:11][C:10]4=[O:18])[NH:37][N:38]=3)=[CH:40][CH:41]=2)[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1

Participants

5

Reactant 3

HCID 178418806HCID 178418806, compoundHCID 178507406HCID 178507406, compoundHCID 178517101HCID 178517101, compound

Product 1

HCID 1785170763-[[[5-[[4-(3-morpholin-4-ylpropoxy)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-morpholin-4-yl-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 (0.017 gms.) is reacted with 0.048 gms. of 5-[4-(3-morpholin-4-yl-propoxy)-benzyl]-2H-pyrazol-3-ylamine by refluxing in tetrahydrofuran (1.0 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-9f2983bfbdb24778bd505c8a6caa9b8d
Source dataset
uspto-grants-2003_05
Patent number
US06559173B1

Reaction notes

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