Hydrochloric Acid → N-[2-(N-{4-[(methoxymethyl)-cyclopropyl]phenyl}carbamoyl)phenyl]-N-(4-pyridylmethyl)-acetamide

HRID 1246965Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1246965
N1[CH:6]=[CH:5][C:4]([CH2:7][CH2:8][C:9]([NH:11][C:12]2[CH:22]=[CH:21][CH:20]=[CH:19][C:13]=2C(OCC)=O)=[O:10])=CC=1.[OH-:23].[Na+].Cl.[CH3:26][O:27][CH2:28][C:29]1([C:33]2[CH:38]=CC(N)=CC=2)CCC1.CCN=C=NC[CH2:46][CH2:47][N:48]([CH3:50])[CH3:49].[CH:51]1[CH:52]=[CH:53][C:54]2N(O)N=[N:57][C:55]=2C=1.CCN(C(C)C)C(C)C>CCO.CN(C=O)C.ClCCl>[CH3:26][O:27][CH2:28][C:29]1([C:20]2[CH:19]=[CH:13][C:12]([NH:11][C:9]([C:8]3[CH:7]=[CH:4][CH:5]=[CH:6][C:49]=3[N:48]([CH2:50][C:53]3[CH:52]=[CH:51][N:57]=[CH:55][CH:54]=3)[C:47](=[O:23])[CH3:46])=[O:10])=[CH:22][CH:21]=2)[CH2:33][CH2:38]1

Komponenten

11

Edukt 7

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 21906959ethyl 2-[N-(4-pyridyl-methyl)acetylamino]benzoateHCID 219069604-[(Methoxymethyl)cyclobutyl]phenylamine

Produkt 1

HCID 21906968N-[2-(N-{4-[(methoxymethyl)-cyclopropyl]phenyl}carbamoyl)phenyl]-N-(4-pyridylmethyl)-acetamide

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 702EthanolLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of ethyl 2-[N-(4-pyridyl-methyl)acetylamino]benzoate (300 mg) and 5 N NaOH (2 ml) in EtOH (20 ml) was stirred at RT for three hours. The solution was neutralized with 5 N HCl and evaporated to dryness. The residue was washed with methanol and filtered. The filtrate was evaporated and the residue was mixed with 4-[(methoxymethyl)cyclobutyl]phenylamine (1 eq), EDCI (1.25 eq), HOBt (1 eq) and DIEA (1.25 eq) in DMF (10 ml) and stirred overnight. The solution was mixed with dichloromethane (80 ml) and washed with water three times followed by brine, dried over Na2SO4 and evaporated, further purified by preparative TLC to give N-[2-(N-{4-[(methoxymethyl)-cyclopropyl]phenyl}carbamoyl)phenyl]-N-(4-pyridylmethyl)-acetamide

Aufarbeitung

  1. customevaporated to dryness
  2. washThe residue was washed with methanol
  3. filtrationfiltered
  4. customThe filtrate was evaporated
  5. stirringstirred overnight
  6. washwashed with water three times
  7. dry with materialdried over Na2SO4
  8. customevaporated
  9. customfurther purified by preparative TLC

Quellen und Nachweise

ORD-Eintrag
ord-197e5a2e6fae42f8a827aab2005eddc5
Quelldatensatz
uspto-grants-2006_10
Patentnummer
US07129252B2

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