Methanol → HCID 178433815, compound

HRID 2271445Notes

Reaction equation

HRID 2271445 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:16]3[CH:25]=[CH:24][C:23]4[CH2:22][CH2:21][CH2:20][CH2:19][C:18]=4[CH:17]=3)[C:14]/2=[O:15])=[CH:6][CH:5]=[CH:4][C:3]=1[C:27]1[O:31][C:30]([C:32]([OH:34])=[O:33])=[CH:29][CH:28]=1.[NH:35]([CH2:37][C@@H:38]([C@H:40]([C@@H:42]([C@@H:44]([CH2:46][OH:47])[OH:45])[OH:43])[OH:41])[OH:39])[CH3:36].[NH:48]([CH2:50][C@@H:51]([C@H:53]([C@@H:55]([C@@H:57]([CH2:59][OH:60])[OH:58])[OH:56])[OH:54])[OH:52])[CH3:49].[OH:61][C:62]1[C:67]([NH:68][N:69]=[C:70]2[C:74](=[O:75])[N:73]([C:76]3[CH:85]=[CH:84][C:83]4[CH2:82][CH2:81][CH2:80][CH2:79][C:78]=4[CH:77]=3)[N:72]=[C:71]2[CH3:86])=[CH:66][CH:65]=[CH:64][C:63]=1[C:87]1[CH:91]=[CH:90][O:89][C:88]=1[C:92]([OH:94])=[O:93].CO>O1CCCC1>[NH:35]([CH2:37][C@@H:38]([C@H:40]([C@@H:42]([C@@H:44]([CH2:46][OH:47])[OH:45])[OH:43])[OH:41])[OH:39])[CH3:36].[NH:48]([CH2:50][C@@H:51]([C@H:53]([C@@H:55]([C@@H:57]([CH2:59][OH:60])[OH:58])[OH:56])[OH:54])[OH:52])[CH3:49].[OH:61][C:62]1[C:67]([NH:68][N:69]=[C:70]2[C:74](=[O:75])[N:73]([C:76]3[CH:85]=[CH:84][C:83]4[CH2:82][CH2:81][CH2:80][CH2:79][C:78]=4[CH:77]=3)[N:72]=[C:71]2[CH3:86])=[CH:66][CH:65]=[CH:64][C:63]=1[C:87]1[CH:91]=[CH:90][O:89][C:88]=1[C:92]([OH:94])=[O:93].[NH:35]([CH2:37][C@@H:38]([C@H:40]([C@@H:42]([C@@H:44]([CH2:46][OH:47])[OH:45])[OH:43])[OH:41])[OH:39])[CH3:36].[NH:35]([CH2:37][C@@H:38]([C@H:40]([C@@H:42]([C@@H:44]([CH2:46][OH:47])[OH:45])[OH:43])[OH:41])[OH:39])[CH3:36].[OH:1][C:2]1[C:7]([NH:8]/[N:9]=[C:10]2/[C:11]([CH3:26])=[N:12][N:13]([C:16]3[CH:25]=[CH:24][C:23]4[CH2:22][CH2:21][CH2:20][CH2:19][C:18]=4[CH:17]=3)[C:14]/2=[O:15])=[CH:6][CH:5]=[CH:4][C:3]=1[C:27]1[O:31][C:30]([C:32]([OH:34])=[O:33])=[CH:29][CH:28]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 178433810HCID 178433810, compoundHCID 178433819HCID 178433819, compound

Product 2

HCID 178433815HCID 178433815, compoundYield 134.9%HCID 178433819HCID 178433819, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(Z)-5-(2-hydroxy-3-{N′-[3-methyl-5-oxo-1-(5,6,7,8-tetrahydro-naphthalen-2-yl)-1,5-dihydro-pyrazol-4-ylidene]-hydrazino}-phenyl)-furan-2-carboxylic acid 7d (100 mg, 0.22 mmol) was suspended in 5 mL of tetrahydrofuran to form a dark red suspension. The reaction mixture was added with meglumine (85 mg, 0.44 mmol), and stirred at room temperature overnight. The resulting solution was added with 4 mL of methanol and concentrated under reduced pressure to obtain the title compound (Z)-5-(2-hydroxy-3-{N′-[3-methyl-5-oxo-1-(5,6,7,8-tetrahydro-naphthalen-2-yl)-1,5-dihydro-pyrazol-4-ylidene]-hydrazino}-phenyl)-furan-2-carboxylic acid bis-(meglumine) 10 (168 mg, yield: 90.8%) as a dark red solid.

Workup

  1. customto form a dark red suspension
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5ce5124f4ccf4b77b743cd2e2227c5de
Source dataset
uspto-grants-2015_09
Patent number
US09120762B2

Reaction notes

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