Sodium Iodide → HCID 66680134, Verbindung

HRID 1626761

Reaktionsgleichung

Reaktionsgleichung von HRID 1626761
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:11][C:12](=[O:15])[CH2:13]Cl)=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[CH:16]([N:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1)([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(N(CC)C(C)C)(C)C.[I-].[Na+]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:11][C:12](=[O:15])[CH2:13][N:32]2[CH2:33][CH2:34][N:29]([CH:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH2:30][CH2:31]2)=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8]

Komponenten

6

Edukt 4

HCID 5238Sodium IodideHCID 70048BenzhydrylpiperazineHCID 81531DiisopropylethylamineHCID 41798255-Chloro-2-((2-chloroacetyl)amino)benzoic acid

Produkt 1

HCID 66680134HCID 66680134, VerbindungAusbeute 11 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

1.0 g (4.0 mmol) of 5-chloro-2-[(chloroacetyl)amino]benzoic acid obtained in Example 72-(i), 1.0 g (4.0 mmol) of 1-benzhydrylpiperazine, 1.1 g (8.8 mmol) of N,N-diisopropylethylamine, and 60 mg (0.4 mmol) of sodium iodide were stirred in 5 mL of DMF solution at 80° C. for 3 hours. Thereafter, the solvent was distilled off under reduced pressure, H2O was added to the residue, and solids were collected by filtration and dried. The obtained crude product was separated and purified by silica gel column chromatography, and the resultant was then recrystallized using ethyl acetate/n-hexane, thereby giving 198 mg of the target 5-chloro-2-({[4-(diphenylmethyl)piperazine-1-yl]acetyl}amino)benzoic acid (yield: 11%).

Aufarbeitung

  1. distillationThereafter, the solvent was distilled off under reduced pressure, H2O
  2. additionwas added to the residue, and solids
  3. filtrationwere collected by filtration
  4. customdried
  5. customThe obtained crude product
  6. customwas separated
  7. custompurified by silica gel column chromatography
  8. customthe resultant was then recrystallized

Quellen und Nachweise

ORD-Eintrag
ord-f5a441c3ef914f4c8480e170a23a89c2
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08785473B2

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