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

HRID 749478ノート

反応式

HRID 749478 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-025febb5de5741d9babe4181f186aeff
出典データセット
uspto-grants-2008_07
特許番号
US07402581B2

反応ノート

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