3-[3-[(2Z)-2-[1-(2,3-dihydro-1H-inden-5-yl)-3-methyl-5-(oxomethylidene)pyrazol-4-ylidene]hydrazinyl]-2-hydroxyphenyl]benzoic acid → 3-[3-[(2Z)-2-[1-(2,3-dihydro-1H-inden-5-yl)-3-methyl-5-(oxomethylidene)pyrazol-4-ylidene]hydrazinyl]-2-hydroxyphenyl]benzoic acid;piperazine

HRID 238701Notes

Reaction equation

HRID 238701 reaction equation
[OH:1][C:2]1[C:7]([NH:8]/[N:9]=[C:10]2\[C:11]([CH3:26])=[N:12][N:13]([C:17]3[CH:18]=[C:19]4[C:23](=[CH:24][CH:25]=3)[CH2:22][CH2:21][CH2:20]4)[C:14]\2=[C:15]=[O:16])=[CH:6][CH:5]=[CH:4][C:3]=1[C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([C:33]([OH:35])=[O:34])[CH:28]=1.[NH:36]1[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]1.[NH:42]1[CH2:47][CH2:46][NH:45][CH2:44][CH2:43]1.[OH:48][C:49]1[C:54]([NH:55]/[N:56]=[C:57]2/[C:58]([CH3:72])=[N:59][N:60]([C:63]3[CH:64]=[C:65]4[C:69](=[CH:70][CH:71]=3)[CH2:68][CH2:67][CH2:66]4)[C:61]/2=[O:62])=[CH:53][CH:52]=[CH:51][C:50]=1[C:73]1[CH:78]=[CH:77][CH:76]=[C:75]([C:79]([OH:81])=[O:80])[CH:74]=1>O1CCCC1>[NH:9]1[CH2:10][CH2:14][NH:13][CH2:17][CH2:18]1.[NH:36]1[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]1.[OH:48][C:49]1[C:54]([NH:55]/[N:56]=[C:57]2/[C:58]([CH3:72])=[N:59][N:60]([C:63]3[CH:64]=[C:65]4[C:69](=[CH:70][CH:71]=3)[CH2:68][CH2:67][CH2:66]4)[C:61]/2=[O:62])=[CH:53][CH:52]=[CH:51][C:50]=1[C:73]1[CH:78]=[CH:77][CH:76]=[C:75]([C:79]([OH:81])=[O:80])[CH:74]=1.[NH:42]1[CH2:47][CH2:46][NH:45][CH2:44][CH2:43]1.[NH:9]1[CH2:10][CH2:14][NH:13][CH2:17][CH2:18]1.[OH:1][C:2]1[C:7]([NH:8]/[N:9]=[C:10]2\[C:11]([CH3:26])=[N:12][N:13]([C:17]3[CH:18]=[C:19]4[C:23](=[CH:24][CH:25]=3)[CH2:22][CH2:21][CH2:20]4)[C:14]\2=[C:15]=[O:16])=[CH:6][CH:5]=[CH:4][C:3]=1[C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([C:33]([OH:35])=[O:34])[CH:28]=1

Participants

5

Reactant 2

HCID 1765211573-[3-[(2Z)-2-[1-(2,3-dihydro-1H-inden-5-yl)-3-methyl-5-(oxomethylidene)pyrazol-4-ylidene]hydrazinyl]-2-hydroxyphenyl]benzoic acidHCID 178420792HCID 178420792, compound

Product 2

HCID 1765266753-[3-[(2Z)-2-[1-(2,3-dihydro-1H-inden-5-yl)-3-methyl-5-(oxomethylidene)pyrazol-4-ylidene]hydrazinyl]-2-hydroxyphenyl]benzoic acid;piperazineYield 185%HCID 178420792HCID 178420792, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(Z)-2′-hydroxy-3′-[N′-(1-indan-5-yl-3-methyl-5-carbonyl-1,5-dihydro-pyrazol-4-ylidene)-hydrazino]-biphenyl-3-carboxylic acid 1j (150 mg, 0.33 mmol) was dissolved in 5 mL of tetrahydrofuran to form a dark red suspension. The reaction mixture was added with piperazine (57 mg, 0.66 mmol) to form a purple solution, and stirred at room temperature for 2 hours. The solid was precipitated from the solution, filtered, then the filter cake was washed with tetrahydrofuran (1 mL×3) and dried in vacuo to obtain the title compound (Z)-2′-hydroxy-3′-[N′-(1-indan-5-yl-3-methyl-5-carbonyl-1,5-dihydro-pyrazol-4-ylidene)-hydrazino]-biphenyl-3-carboxylic acid bis-(piperazine) 3 (130 mg, yield: 62.8%) as a dark red solid.

Workup

  1. customto form a dark red suspension
  2. customto form a purple solution
  3. customThe solid was precipitated from the solution
  4. filtrationfiltered
  5. washthe filter cake was washed with tetrahydrofuran (1 mL×3)
  6. customdried in vacuo

Sources & evidence

ORD record
ord-634e4e27a065455bb63b5e87d48fbdb3
Source dataset
uspto-grants-2014_02
Patent number
US08642637B2

Reaction notes

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