4-Fluorophenylhydrazine hydrochloride → 2-[(4-{2-[[1-(4-fluorophenyl)-3-methyl-1H-pyrazol-5-yl](heptyl)amino]ethyl}-1,3-thiazol-2-yl)thio]-2-methylpropionic acid

HRID 914376Notes

Reaction equation

HRID 914376 reaction equation
C([O:5][C:6](=[O:32])[C:7]([S:10][C:11]1[S:12][CH:13]=[C:14]([CH2:16][CH2:17][N:18]([C:26](=O)[CH2:27][C:28]([CH3:30])=O)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[N:15]=1)([CH3:9])[CH3:8])(C)(C)C.Cl.[F:34][C:35]1[CH:40]=[CH:39][C:38]([NH:41][NH2:42])=[CH:37][CH:36]=1.C([O-])(=O)C.[Na+]>>[F:34][C:35]1[CH:40]=[CH:39][C:38]([N:41]2[C:26]([N:18]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH2:17][CH2:16][C:14]3[N:15]=[C:11]([S:10][C:7]([CH3:8])([CH3:9])[C:6]([OH:5])=[O:32])[S:12][CH:13]=3)=[CH:27][C:28]([CH3:30])=[N:42]2)=[CH:37][CH:36]=1

Participants

4

Reactant 3

HCID 699814-Fluorophenylhydrazine hydrochlorideHCID 517045Sodium AcetateHCID 866213012-[(4-{2-[Acetoacetyl(heptyl)amino]ethyl}-1,3-thiazol-2-yl)thio]-2-methylpropionic acid tert-butyl ester

Product 1

HCID 597592212-[(4-{2-[[1-(4-fluorophenyl)-3-methyl-1H-pyrazol-5-yl](heptyl)amino]ethyl}-1,3-thiazol-2-yl)thio]-2-methylpropionic acid

Procedure

A compound obtained using 2-[(4-{2-[acetoacetyl(heptyl)amino]ethyl}-1,3-thiazol-2-yl)thio]-2-methylpropionic acid tert-butyl ester synthesized in Example 446-1, and (4-fluorophenyl)hydrazine hydrochloride and sodium acetate for neutralization, and by an operation similar to that of Example 446 was purified by silica gel chromatography (elution solvent; chloroform:methanol=10:1) to give the title compound.

Workup

  1. customA compound obtained
  2. customby an operation similar to that of Example 446 was purified by silica gel chromatography (elution solvent; chloroform:methanol=10:1)

Sources & evidence

ORD record
ord-c1a9083a2c79413784b02123fa9c64d0
Source dataset
uspto-grants-2011_09
Patent number
US08026370B2

Reaction notes

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