Phenyl pyridin-3-ylcarbamate → 4-Quinolin-3-ylmethyl-piperazine-1-carboxylic acid pyridin-3-ylamide

HRID 40593

반응식

HRID 40593 반응식
C1(O[C:8](=[O:16])[NH:9][C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)C=CC=CC=1.[N:17]1([CH2:23][C:24]2[CH:25]=[N:26][C:27]3[C:32]([CH:33]=2)=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1>CS(C)=O>[N:12]1[CH:13]=[CH:14][CH:15]=[C:10]([NH:9][C:8]([N:20]2[CH2:21][CH2:22][N:17]([CH2:23][C:24]3[CH:25]=[N:26][C:27]4[C:32]([CH:33]=3)=[CH:31][CH:30]=[CH:29][CH:28]=4)[CH2:18][CH2:19]2)=[O:16])[CH:11]=1

참가 물질

4

반응물 2

HCID 6935890Phenyl pyridin-3-ylcarbamateHCID 578808813-[(Piperazin-1-yl)methyl]quinoline

생성물 1

HCID 116959414-Quinolin-3-ylmethyl-piperazine-1-carboxylic acid pyridin-3-ylamide수율 80%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

A solution of pyridin-3-yl-carbamic acid phenyl ester (0.3 g) and 3-piperazin-1-ylmethyl-quinoline (0.32 g) in DMSO (0.5 mL) was heated in a microwave reactor at 100° C. for 0.5 h. The reaction mixture was partitioned between DCM and water. The combined organic layers were washed with brine (3×), dried (Na2SO4), and concentrated. The residue was purified by column chromatography to yield the title compound as a beige solid (80%). 1H NMR (400 MHz, CDCl3): 8.92 (d, J=2.3 Hz, 1H), 8.72 (d, J=2.3 Hz, 1H), 8.28 (d, J=8.1 Hz, 1H), 8.23-8.21 (m, 1H), 8.13-8.10 (m, 2H), 7.84-7.82 (m, 1H), 7.74-7.70 (m, 1H), 7.59-7.55 (m, 1H), 7.37-7.34 (m, 2H), 3.77 (s, 2H), 3.64-3.62 (m, 4H), 2.62-2.59 (m, 4H).

후처리

  1. customThe reaction mixture was partitioned between DCM and water
  2. washThe combined organic layers were washed with brine (3×)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography

출처 및 근거

ORD 기록
ord-1da7301c91db417887e290fa42a65101
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08530476B2

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