Aniline → N-ethyl-N-isopropylpropan-2-amine 2-(4-(methoxycarbonyl)phenyl)-2-(phenylamino)acetate

HRID 1255051노트

반응식

HRID 1255051 반응식
Br[CH:2]([C:6]1[CH:11]=[CH:10][C:9]([C:12]([O:14][CH3:15])=[O:13])=[CH:8][CH:7]=1)[C:3]([OH:5])=[O:4].[NH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[CH3:23][CH2:24][N:25]([CH:29]([CH3:31])[CH3:30])[CH:26]([CH3:28])[CH3:27]>C(#N)C>[CH3:15][O:14][C:12]([C:9]1[CH:10]=[CH:11][C:6]([CH:2]([NH:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:3]([OH:5])=[O:4])=[CH:7][CH:8]=1)=[O:13].[CH2:24]([N:25]([CH:29]([CH3:31])[CH3:30])[CH:26]([CH3:28])[CH3:27])[CH3:23]

참가 물질

5

반응물 3

HCID 6115AnilineHCID 81531DiisopropylethylamineHCID 59401242HCID 59401242, 화합물

생성물 1

HCID 67425011N-ethyl-N-isopropylpropan-2-amine 2-(4-(methoxycarbonyl)phenyl)-2-(phenylamino)acetate수율 37%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
100 °C

실험 절차

2-Bromo-2-(4-(methoxycarbonyl)phenyl)acetic acid (700 mg, 2.56 mmol), aniline (0.23 mL, 2.56 mmol), and DIPEA (0.94 mL, 5.38 mmol) are dissolved in acetonitrile (5 mL). The reaction is stirred at 100° C. under microwave irradiation for 15 minutes. Acetonitrile is evaporated and the residue is dissolved in DCM and washed with water and brine. The organic layer is dried (Na2SO4), filtered and evaporated. The crude compound is purified by flash chromatography (DCM/MeOH=9/1) to obtain intermediate I142 as a white solid (381 mg, 37% yield).

후처리

  1. customAcetonitrile is evaporated
  2. dissolutionthe residue is dissolved in DCM
  3. washwashed with water and brine
  4. dry with materialThe organic layer is dried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude compound is purified by flash chromatography (DCM/MeOH=9/1)

출처 및 근거

ORD 기록
ord-83a3399676454637bc46af66c33cb0bb
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08455646B2

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