Triethylamine → 6-cyano-N-[(2S)-2-(4-fluorophenyl)pent-4-en-1-yl]-N-methylindane-4-carboxamide

HRID 749478노트

반응식

HRID 749478 반응식
[C:1]([C:3]1[CH:4]=[C:5]([C:12]([OH:14])=O)[C:6]2[CH2:7][CH2:8][CH2:9][C:10]=2[CH:11]=1)#[N:2].C(Cl)(=O)C(Cl)=O.[F:21][C:22]1[CH:27]=[CH:26][C:25]([C@H:28]([CH2:32][CH:33]=[CH2:34])[CH2:29][NH:30][CH3:31])=[CH:24][CH:23]=1.C(N(CC)CC)C>CN(C=O)C.C(Cl)Cl>[C:1]([C:3]1[CH:4]=[C:5]([C:12]([N:30]([CH2:29][C@H:28]([C:25]2[CH:24]=[CH:23][C:22]([F:21])=[CH:27][CH:26]=2)[CH2:32][CH:33]=[CH2:34])[CH3:31])=[O:14])[C:6]2[CH2:7][CH2:8][CH2:9][C:10]=2[CH:11]=1)#[N:2]

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 15536023[(2S)-2-(4-Fluorophenyl)pent-4-en-1-yl]methylamineHCID 689791816-Cyanoindane-4-carboxylic acid

생성물 1

HCID 689790206-cyano-N-[(2S)-2-(4-fluorophenyl)pent-4-en-1-yl]-N-methylindane-4-carboxamide수율 62.1%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

실험 절차

6-Cyanoindane-4-carboxylic acid (150 mg, 0.8 mmol) and oxalyl chloride (130 mg, 1.0 mmol) were mixed with CH2Cl2 (20 mL) whereupon DMF (100 mg) was added. After 1 h at room temperature [(2S)-2-(4-fluorophenyl)pent-4-en-1-yl]methylamine (Bioorg. Med. Chem. Lett; 2001; 265-270; 200 mg, 1.0 mmol) and triethylamine (200 mg, 2.0 mmol) were added to the mixture in the given order. The mixture was stirred at room temperature for 20 min and then the solvent was evaporated. The product was purified by chromatography on silica gel using hexane and ethyl acetate (1:1). There was obtained 180 mg (62%) of 6-cyano-N-[(2S)-2-(4-fluorophenyl)pent-4-en-1-yl]-N-methylindane-4-carboxamide as an oil. 1H NMR (300 MHz, CDCl3): 2.0-2.1 (m, 2H), 2.2 (t, 1H), 2.4 (m, 2H), 2.6 (s, 4H), 2.8-3.4 (m, 4H), 3.7 (dd, 1H), 3.8-3.9 (dd, 1H), 4.9-5.1 (m, 2H), 5.4-5.8 (m, 1H), 6.8-7.1 (m, 4H), 7.2 (m, 1H), 7.5 (s, 1H).

후처리

  1. additionwas added
  2. customthe solvent was evaporated
  3. customThe product was purified by chromatography on silica gel

출처 및 근거

ORD 기록
ord-025febb5de5741d9babe4181f186aeff
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07402581B2

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