Benzylamine → HCID 24959697、化合物

HRID 2381854ノート

反応式

HRID 2381854 の反応式
[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

参加物

8

反応物 5

HCID 7504BenzylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 24959696HCID 24959696、化合物

生成物 1

HCID 24959697HCID 24959697、化合物収率 10%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-3387355b49ac42c08d159314524ee0fc
出典データセット
uspto-grants-2012_09
特許番号
US08258160B2

反応ノート

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