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

HRID 1246965Notes

Reaction equation

HRID 1246965 reaction equation
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

Participants

11

Reactant 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

Product 1

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

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

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

Workup

  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

Sources & evidence

ORD record
ord-197e5a2e6fae42f8a827aab2005eddc5
Source dataset
uspto-grants-2006_10
Patent number
US07129252B2

Reaction notes

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