Pyridine → N-Benzyl-4-methyl-2-(5-phenylpentanamido)thiazole-5-carboxamide

HRID 45379노트

반응식

HRID 45379 반응식
[CH2:1]([NH:8][C:9]([C:11]1[S:15][C:14]([NH2:16])=[N:13][C:12]=1[CH3:17])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.[C:24]1([CH2:30][CH2:31][CH2:32][CH2:33][C:34](Cl)=[O:35])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>O1CCCC1.ClCCl.CN(C1C=CC=CN=1)C>[CH2:1]([NH:8][C:9]([C:11]1[S:15][C:14]([NH:16][C:34](=[O:35])[CH2:33][CH2:32][CH2:31][CH2:30][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[N:13][C:12]=1[CH3:17])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

7

반응물 3

HCID 1049PyridineHCID 210824N-Benzyl-2-imino-4-methyl-2,3-dihydro-1,3-thiazole-5-carboximidic acidHCID 109654605-phenylpentanoyl Chloride

생성물 1

HCID 59369684N-Benzyl-4-methyl-2-(5-phenylpentanamido)thiazole-5-carboxamide수율 98.2%

시약·촉매·용매 3

HCID 218852-Dimethylaminopyridine촉매HCID 6344Dichloromethane용매2회HCID 8028Tetrahydrofuran용매

실험 절차

To a cooled mixture of 2-amino-4-methylthiazole-5-carboxylic acid benzylamide (0.10 g, 0.40 mmol), pyridine (0.096 g, 1.21 mmol), and dimethylaminopyridine (0.010 mg) in anhydrous tetrahydrofuran (5 mL) was added 5-phenylpentanoyl chloride (0.16 g, 0.81 mmol) in anhydrous dichloromethane (1 mL) dropwise. The reaction mixture was stirred at ambient temperature for 2 hours, then diluted with dichloromethane (10 mL) and washed with saturated sodium bicarbonate solution (2×5 mL), 1 N hydrochloric acid (5 mL), and brine (5 mL). The organic phase was dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrate in vacuo. The residue was purified by column chromatography over silica gel, eluting with ethyl acetate/hexanes (1/1) to afford the title compound as a clear oil (0.16 g, 97%) %); 1H NMR (CDCl3, 300 MHz) δ 11.19 (s, br, 1H), 7.33-7.09 (m, 10H), 6.40 (t, J=4.8 Hz, 1H), 4.58 (d, J=5.8 Hz, 2H), 2.60-2.39 (m, 7H), 1.74-1.56 (m, 4H); MS (ES+) m/z 408.6 (M+1).

후처리

  1. washwashed with saturated sodium bicarbonate solution (2×5 mL), 1 N hydrochloric acid (5 mL), and brine (5 mL)
  2. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrate in vacuo
  5. customThe residue was purified by column chromatography over silica gel
  6. washeluting with ethyl acetate/hexanes (1/1)

출처 및 근거

ORD 기록
ord-d47a195e5c63486b8f9d6aa68013c626
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08541457B2

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