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

HRID 749478Notes

Reaction equation

HRID 749478 reaction equation
[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]

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-025febb5de5741d9babe4181f186aeff
Source dataset
uspto-grants-2008_07
Patent number
US07402581B2

Reaction notes

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