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Triethylamine → 4-bromo-N-(2,4-dimethoxybenzyl) N-(3-(4-nitrophenyl)prop-2-ynyl)-1H-pyrrole-2-carboxamide

HRID 2096279
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HRID 2096279 반응식
[CH3:1][O:2][C:3]1[CH:22]=[C:21]([O:23][CH3:24])[CH:20]=[CH:19][C:4]=1[CH2:5][NH:6][CH2:7][C:8]#[C:9][C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=1.[Br:25][C:26]1[CH:27]=[C:28]([C:31](O)=[O:32])[NH:29][CH:30]=1.Cl.C(N=C=NCCCN(C)C)C.O.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C>CN(C)C=O>[Br:25][C:26]1[CH:27]=[C:28]([C:31]([N:6]([CH2:5][C:4]2[CH:19]=[CH:20][C:21]([O:23][CH3:24])=[CH:22][C:3]=2[O:2][CH3:1])[CH2:7][C:8]#[C:9][C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=2)=[O:32])[NH:29][CH:30]=1
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참가 물질

7

반응물 5

HCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27413814-bromo-1H-pyrrole-2-carboxylic acidHCID 27960291-Hydroxybenzotriazole hydrateHCID 67443629N-(2,4-dimethoxybenzyl)-3-(4-nitrophenyl)prop-2-yn-1-amine

생성물 1

HCID 67441092
4-bromo-N-(2,4-dimethoxybenzyl) N-(3-(4-nitrophenyl)prop-2-ynyl)-1H-pyrrole-2-carboxamide

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of EXAMPLE 23B (1 g, 3.07 mmol) in anhydrous N,N-dimethylformamide (25 mL) was added 4-bromo-1H-pyrrole-2-carboxylic acid (0.67 g, 3.53 mmol), 1-ethyl-3-[3-(dimethylamino)propyl]-carbodiimide hydrochloride (0.77 g, 4 mmol), 1-hydroxybenzotriazole hydrate (0.61 g, 4 mmol) and triethylamine (0.4 g, 4 mmol). The reaction was stirred at room temperature overnight, and partitioned between ethyl acetate and brine. The organic phase was washed with brine, dried over anhydrous Na2SO4, filtered, and concentrated. The crude material was purified flash chromatography (20% ethyl acetate in hexane) to afford the title compound. LC-MS (ESI): m/z 500, 498 (M+H), RT: 2.37 min; 1H NMR (400 MHz, dimethylsulfoxide-d6): δ 3.75 (s, 3H), 3.78 (s, 3H), 4.51 (s, 2H), 4.77 (s, 2H), 6.53 (dd, J=6.4, 2.0 Hz, 1H), 6.60 (d, J=2.0 Hz, 1H), 7.09 (dd, J=1.2, 1.6 Hz, 1H), 7.15 (d, J=8.0 Hz, 1H), 7.60 (d, J=8.8 Hz, 2H), 8.21 (d, J=9.2 Hz, 2H), 12.02 (br s, 1H).

후처리

  1. custompartitioned between ethyl acetate and brine
  2. washThe organic phase was washed with brine
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude material was purified flash chromatography (20% ethyl acetate in hexane)

출처 및 근거

ORD 기록
ord-f9400102b1c54a09842c530e4bb8e1a6
출처 데이터셋
uspto-grants-2013_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08450320B2

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