3-Methylbenzaldehyde → 5-{1-[4-(3-Methyl-benzylamino)-phenyl]-ethylcarbamoyl}-thiophene-2-carboxylic acid methyl ester

HRID 30236

반응식

HRID 30236 반응식
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:10](=[O:21])[NH:11][CH:12]([C:14]2[CH:19]=[CH:18][C:17]([NH2:20])=[CH:16][CH:15]=2)[CH3:13])=[CH:8][CH:9]=1)=[O:4].[C:22]1([CH3:30])[CH:27]=[CH:26][CH:25]=[C:24]([CH:28]=O)[CH:23]=1.C([BH3-])#N.[Na+].[Cl-].[NH4+]>O.C1COCC1.C(O)C>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:10](=[O:21])[NH:11][CH:12]([C:14]2[CH:15]=[CH:16][C:17]([NH:20][CH2:30][C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([CH3:28])[CH:23]=3)=[CH:18][CH:19]=2)[CH3:13])=[CH:8][CH:9]=1)=[O:4]

참가 물질

8

반응물 4

HCID 121053-MethylbenzaldehydeHCID 25517Ammonium ChlorideHCID 5003444Sodium cyanoborohydrideHCID 691350895-[1-(4-Amino-phenyl)-ethylcarbamoyl]-thiophene-2-carboxylic acid methyl ester

생성물 1

HCID 691344495-{1-[4-(3-Methyl-benzylamino)-phenyl]-ethylcarbamoyl}-thiophene-2-carboxylic acid methyl ester수율 43%

시약·촉매·용매 3

HCID 702Ethanol용매HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

A mixture of 304.0 mg (1.0 mmol) 5-[1-(4-amino-phenyl)-ethylcarbamoyl]-thiophene-2-carboxylic acid methyl ester, 120.0 mg (1.0 mmol) m-tolualdehyde and 2 ml ethanol was heated under reflux for 1 h. The solvent was evaporated and 3 ml THF and 315 mg (5.0 mmol) sodium cyanoborohydride were added to the residue. After 18 h 5 ml aqueous ammonium chloride solution and 10 ml water were added. The aqueous phase was extracted with dichloromethane, the combined organic phases were dried over magnesium sulfate, the solvent was evaporated and the residue subjected to silica gel chromatography (ethyl acetate/petrol ether 1:1) to yield 175 mg (0.43 mmol) 5-{1-[4-(3-Methyl-benzylamino)-phenyl]-ethylcarbamoyl}-thiophene-2-carboxylic acid methyl ester.

후처리

  1. temperaturewas heated
  2. temperatureunder reflux for 1 h
  3. customThe solvent was evaporated
  4. extractionThe aqueous phase was extracted with dichloromethane
  5. dry with materialthe combined organic phases were dried over magnesium sulfate
  6. customthe solvent was evaporated

출처 및 근거

ORD 기록
ord-438e5106c59f43a0b80eee81d9de075a
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07423060B2

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