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Triethylamine → (E)-N-[2-[(2-Methyl-4-quinolyl)amino]ethyl]but-2-enamide

HRID 333098
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HRID 333098 반응식
C[CH:2](C)/[CH:3]=[CH:4]/[C:5](O)=[O:6].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:33][C:34]1[CH:43]=[C:42]([NH:44][CH2:45][CH2:46][NH2:47])[C:41]2[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=2)[N:35]=1.C(N(CC)CC)C>C(#N)C>[CH3:33][C:34]1[CH:43]=[C:42]([NH:44][CH2:45][CH2:46][NH:47][C:5](=[O:6])/[CH:4]=[CH:3]/[CH3:2])[C:41]2[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=2)[N:35]=1
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참가 물질

6

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HCID 8471TriethylamineHCID 6420393-Isopropyl acrylic acidHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 6471895N1-(2-Methylquinolin-4-yl)ethane-1,2-diamine

생성물 1

HCID 86691181(E)-N-[2-[(2-Methyl-4-quinolyl)amino]ethyl]but-2-enamide수율 68.3%

시약·촉매·용매

1
HCID 6342Acetonitrile용매

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온도
0 °C

실험 절차

(E)-4-Methylpent-2-enoic acid (190 mg, 1.3 mmol) was mixed together with HBTU (470 mg, 1.3 mmol) and N-(2-methyl-4-quinolyl)ethane-1,2-diamine (250 mg, 1.2 mmol) in acetonitrile (5 ml). Triethylamine (1 mll) was added with stirring at 0° C. over 15 minutes and the resulting mixture was stirred at room temperature overnight. The volatiles were removed under reduced pressure, the residue was dissolved in DCM and washed with a saturated solution of sodium bicarbonate. The combined aqueous solutions were extracted three times with DCM. The organic layers were combined, dried over sodium sulfate, the solvent was removed under reduced pressure to give 245 mg of a yellow solid (0.82 mmol, 66%). MS (APCI) m/z=298.2 [M+1]+.

후처리

  1. stirringthe resulting mixture was stirred at room temperature overnight
  2. customThe volatiles were removed under reduced pressure
  3. dissolutionthe residue was dissolved in DCM
  4. washwashed with a saturated solution of sodium bicarbonate
  5. extractionThe combined aqueous solutions were extracted three times with DCM
  6. dry with materialdried over sodium sulfate
  7. customthe solvent was removed under reduced pressure

출처 및 근거

ORD 기록
ord-5f64f7331f114d09a892ddee5f9bd4b8
출처 데이터셋
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08877934B2

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