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

HRID 1246965노트

반응식

HRID 1246965 반응식
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

참가 물질

11

반응물 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

생성물 1

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

시약·촉매·용매 3

HCID 702Ethanol용매HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

실험 절차

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

후처리

  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

출처 및 근거

ORD 기록
ord-197e5a2e6fae42f8a827aab2005eddc5
출처 데이터셋
uspto-grants-2006_10
특허 번호
US07129252B2

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