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

HRID 238700Notes

Reaction equation

HRID 238700 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.[CH2:36]([CH2:38][NH2:39])[OH:37].[CH2:40]([CH2:42][NH2:43])[OH:41].[OH:44][C:45]1[C:50]([NH:51]/[N:52]=[C:53]2/[C:54]([CH3:68])=[N:55][N:56]([C:59]3[CH:60]=[C:61]4[C:65](=[CH:66][CH:67]=3)[CH2:64][CH2:63][CH2:62]4)[C:57]/2=[O:58])=[CH:49][CH:48]=[CH:47][C:46]=1[C:69]1[CH:74]=[CH:73][CH:72]=[C:71]([C:75]([OH:77])=[O:76])[CH:70]=1>O1CCCC1>[CH2:2]([CH2:7][NH2:8])[OH:1].[CH2:36]([CH2:38][NH2:39])[OH:37].[OH:44][C:45]1[C:50]([NH:51]/[N:52]=[C:53]2/[C:54]([CH3:68])=[N:55][N:56]([C:59]3[CH:60]=[C:61]4[C:65](=[CH:66][CH:67]=3)[CH2:64][CH2:63][CH2:62]4)[C:57]/2=[O:58])=[CH:49][CH:48]=[CH:47][C:46]=1[C:69]1[CH:74]=[CH:73][CH:72]=[C:71]([C:75]([OH:77])=[O:76])[CH:70]=1.[CH2:40]([CH2:42][NH2:43])[OH:41].[CH2:2]([CH2:7][NH2:8])[OH: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 178433792HCID 178433792, compound

Product 2

HCID 176521156bis(2-aminoethanol);3-[3-[(2Z)-2-[1-(2,3-dihydro-1H-inden-5-yl)-3-methyl-5-(oxomethylidene)pyrazol-4-ylidene]hydrazinyl]-2-hydroxyphenyl]benzoic acidYield 281.8%HCID 178433792HCID 178433792, 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 (454 mg, 1.0 mmol) was dissolved in 16 mL of tetrahydrofuran. The reaction mixture was added with ethanolamine (143 mg, 2.35 mmol), and stirred for 3 hours. The mixture was filtered, the filter cake was washed with tetrahydrofuran (2 mL×3), and the solid was 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-(ethanolamine) 1 (553 mg, yield: 96.0%) as a dark red solid.

Workup

  1. filtrationThe mixture was filtered
  2. washthe filter cake was washed with tetrahydrofuran (2 mL×3)
  3. customthe solid was dried in vacuo

Sources & evidence

ORD record
ord-6d81e27821f44637ae1288faf4a7ffb9
Source dataset
uspto-grants-2014_02
Patent number
US08642637B2

Reaction notes

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