Benzylamine → HCID 24959697, 화합물

HRID 2381854노트

반응식

HRID 2381854 반응식
[CH3:1][C:2]1[CH:6]=[C:5]([N:7]2[N:11]=[N:10][C:9]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[N:8]2)[S:4][C:3]=1[C:18]([OH:20])=O.ON1C2C=CC=CC=2N=N1.CN(C)CCCN=C=NCC.C(N(CC)C(C)C)(C)C.[CH2:51]([NH2:58])[C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1>CN(C)C=O.ClCCl>[CH2:51]([NH:58][C:18]([C:3]1[S:4][C:5]([N:7]2[N:11]=[N:10][C:9]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)=[N:8]2)=[CH:6][C:2]=1[CH3:1])=[O:20])[C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1

참가 물질

8

반응물 5

HCID 7504BenzylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 24959696HCID 24959696, 화합물

생성물 1

HCID 24959697HCID 24959697, 화합물수율 10%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

실험 절차

To a solution of 3-methyl-5-(5-phenyl-2H-tetrazol-2-yl)thiophene-2-carboxylic acid (0.12 g, 0.40 mmol) in anhydrous N,N-dimethylformamide (5 mL) was added 1-hydroxybenzotriazole (0.65 g, 0.48 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide (0.09 g, 0.48 mmol), N,N-diisopropylethylamine (0.21 mL, 1.20 mmol) and benzylamine (0.05 mL, 0.48 mmol). The reaction mixture was stirred at ambient temperature for 18 hours, diluted with dichloromethane (30 mL) and washed with saturated aqueous sodium bicarbonate (5 mL) and brine (5 mL). The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography to afford the title compound as a white solid in 10% yield (0.02 g): mp 155-158° C. (ethyl acetate/hexanes); 1H NMR (300 MHz, CDCl3) δ 8.23-8.19 (m, 2H), 7.53-7.51 (m, 4H), 7.39-7.35 (m, 5H), 6.09 (br s, 1H), 4.65 (d, J=6.0, 2H), 2.58 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 165.4, 161.9, 140.1, 137.6, 130.9, 129.1, 129.0, 128.9, 128.8, 127.9, 127.8, 127.1, 126.4, 122.7, 44.3, 16.2; MS (ES+) m/z 376.3 (M+1).

후처리

  1. washwashed with saturated aqueous sodium bicarbonate (5 mL) and brine (5 mL)
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography

출처 및 근거

ORD 기록
ord-3387355b49ac42c08d159314524ee0fc
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08258160B2

반응 노트

불러오는 중…