HCID 178433880, compound → HCID 178433881, compound

HRID 2420668Notes

Reaction equation

HRID 2420668 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([N:9]2[N:32]=[C:31]([CH3:33])/[C:12](=[N:13]/[NH:14][C:15]3[CH:16]=[CH:17][CH:18]=[C:19]([C:22]4[CH:23]=[CH:24][CH:25]=[C:26]([C:28]([OH:30])=[O:29])[CH:27]=4)[C:20]=3[OH:21])/[C:10]2=[O:11])=[CH:6][C:7]=1[CH3:8]>C(O)(=O)C>[CH3:8][C:7]1[CH:6]=[C:5]([N:9]2[C:10](=[O:11])[C:12](=[N:13][NH:14][C:15]3[C:20]([OH:21])=[C:19]([C:22]4[CH:23]=[CH:24][CH:25]=[C:26]([C:28]([OH:30])=[O:29])[CH:27]=4)[CH:18]=[CH:17][CH:16]=3)[C:31]([CH3:33])=[N:32]2)[CH:4]=[CH:3][C:2]=1[CH3:1]

Participants

3

Reactant 1

HCID 178433880HCID 178433880, compound

Product 1

HCID 178433881HCID 178433881, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
40 °C

Procedure

Crude Eltrombopag (151 g, HPLC purity: 98.5%) was suspended in 2.9 L of glacial acetic acid in 3 L reactor. The suspension was stirred for five hours under reflux and cooled to 40° C. Crystals formed and were filtrated off, washed with 200 mL of methanol:water (1:1) and dried at 60° C./0 mbar overnight yielding 133 g orange solid of pure 3′-{N′-[1-(3,4-Dimethylphenyl)-3-methyl-5-oxo-1,5-dihydro-pyrazol-4-ylidene]hydrazino}-2′-hydroxybiphenyl-3-carboxylic acid (HPLC: 99.8%; XRPD: form I) (Yield=88%). PXRD analysis provided the diffractogram as shown in FIG. 1. DSC analysis provided the thermogram as shown in FIG. 2

Workup

  1. temperatureunder reflux
  2. customCrystals formed
  3. filtrationwere filtrated off
  4. washwashed with 200 mL of methanol:water (1:1)
  5. customdried at 60° C./0 mbar overnight

Sources & evidence

ORD record
ord-fb04ad4603894b169ea4fa7241012b0c
Source dataset
uspto-grants-2011_06
Patent number
US07956048B2

Reaction notes

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