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;bis(N-ethylethanamine)

HRID 2271434Notes

Reaction equation

HRID 2271434 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]([NH:38][CH2:39][CH3:40])[CH3:37].[CH2:41]([NH:43][CH2:44][CH3:45])[CH3:42].[OH:46][C:47]1[C:52]([NH:53]/[N:54]=[C:55]2/[C:56]([CH3:70])=[N:57][N:58]([C:61]3[CH:62]=[C:63]4[C:67](=[CH:68][CH:69]=3)[CH2:66][CH2:65][CH2:64]4)[C:59]/2=[O:60])=[CH:51][CH:50]=[CH:49][C:48]=1[C:71]1[CH:76]=[CH:75][CH:74]=[C:73]([C:77]([OH:79])=[O:78])[CH:72]=1>O1CCCC1>[CH2:14]([NH:13][CH2:17][CH3:25])[CH3:10].[CH2:36]([NH:38][CH2:39][CH3:40])[CH3:37].[OH:46][C:47]1[C:52]([NH:53]/[N:54]=[C:55]2/[C:56]([CH3:70])=[N:57][N:58]([C:61]3[CH:62]=[C:63]4[C:67](=[CH:68][CH:69]=3)[CH2:66][CH2:65][CH2:64]4)[C:59]/2=[O:60])=[CH:51][CH:50]=[CH:49][C:48]=1[C:71]1[CH:76]=[CH:75][CH:74]=[C:73]([C:77]([OH:79])=[O:78])[CH:72]=1.[CH2:41]([NH:43][CH2:44][CH3:45])[CH3:42].[CH2:14]([NH:13][CH2:17][CH3:25])[CH3:10].[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 178433791HCID 178433791, compound

Product 2

HCID 1765360193-[3-[(2Z)-2-[1-(2,3-dihydro-1H-inden-5-yl)-3-methyl-5-(oxomethylidene)pyrazol-4-ylidene]hydrazinyl]-2-hydroxyphenyl]benzoic acid;bis(N-ethylethanamine)Yield 195.8%HCID 178433791HCID 178433791, 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 solution. The solution was added dropwise with diethylamine (48 mg, 0.66 mmol) to form a purple solution and stirred for 2 hours. The solid was precipitated from the solution. The mixture was filtered, the filter cake was washed with tetrahydrofuran (1 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-(diethylamine) 2 (132 mg, yield: 66.7%) as a red solid.

Workup

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

Sources & evidence

ORD record
ord-ea9e187218a54dfa830bf8ee6bb13526
Source dataset
uspto-grants-2015_09
Patent number
US09120762B2

Reaction notes

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