Diisopropylethylamine → 3-cyano-N-ethyl-N-[(2S)-2-(4-fluorophenyl)pent-4-en-1-yl]-5,6,7,8-tetrahydronaphthalene-1-carboxamide

HRID 749459Notes

Reaction equation

HRID 749459 reaction equation
[CH2:1]([NH:3][CH2:4][C@H:5]([C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=1)[CH2:6][CH:7]=[CH2:8])[CH3:2].CCN(C(C)C)C(C)C.[C:25]([C:27]1[CH:28]=[C:29]([C:37](Cl)=[O:38])[C:30]2[CH2:31][CH2:32][CH2:33][CH2:34][C:35]=2[CH:36]=1)#[N:26]>C(Cl)Cl>[C:25]([C:27]1[CH:28]=[C:29]([C:37]([N:3]([CH2:1][CH3:2])[CH2:4][C@H:5]([C:9]2[CH:10]=[CH:11][C:12]([F:15])=[CH:13][CH:14]=2)[CH2:6][CH:7]=[CH2:8])=[O:38])[C:30]2[CH2:31][CH2:32][CH2:33][CH2:34][C:35]=2[CH:36]=1)#[N:26]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 224526673-Cyano-5,6,7,8-tetrahydronaphthalene-1-carbonyl chlorideHCID 68978108(2S)-N-ethyl-2-(4-fluorophenyl)pent-4-en-1-amine

Product 1

HCID 689787003-cyano-N-ethyl-N-[(2S)-2-(4-fluorophenyl)pent-4-en-1-yl]-5,6,7,8-tetrahydronaphthalene-1-carboxamideYield 53%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

(2S)-N-Ethyl-2-(4-fluorophenyl)pent-4-en-1-amine (0.13 g, 0.63 mmol) was dissolved in CH2Cl2 and to the solution were added DIPEA (0.18 g, 1.4 mmol) and then 3-cyano-5,6,7,8-tetrahydronaphthalene-1-carbonyl chloride (see WO 00/34243; 0.15 g, 0.66 mmol) dissolved in CH2Cl2 (2 mL). The mixture was stirred for 2 h at room temperature and then diluted with CH2Cl2. The solution was washed with water, aqueous KHSO4 (10 mL, 1M) and brine. The solvent was removed by evaporation after the solution had been dried. The product was purified by chromatagraphy on silica gel using a gradient of methanol-CH2Cl2 (0% methanol-5% methanol). There was obtained 0.13 g (53%) of 3-cyano-N-ethyl-N-[(2S)-2-(4-fluorophenyl)pent-4-en-1-yl]-5,6,7,8-tetrahydronaphthalene-1-carboxamide as an oil.

Workup

  1. washThe solution was washed with water, aqueous KHSO4 (10 mL, 1M) and brine
  2. customThe solvent was removed by evaporation after the solution
  3. customhad been dried
  4. customThe product was purified by chromatagraphy on silica gel using a gradient of methanol-CH2Cl2 (0% methanol-5% methanol)

Sources & evidence

ORD record
ord-48860976052a40969d082906d55efad2
Source dataset
uspto-grants-2008_07
Patent number
US07402581B2

Reaction notes

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