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

HRID 1246965ノート

反応式

HRID 1246965 の反応式
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

参加物

11

反応物 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

生成物 1

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

試薬・触媒・溶媒 3

HCID 702Ethanol溶媒HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

実験手順

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

後処理

  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

出典と根拠

ORDレコード
ord-197e5a2e6fae42f8a827aab2005eddc5
出典データセット
uspto-grants-2006_10
特許番号
US07129252B2

反応ノート

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