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

HRID 749450ノート

反応式

HRID 749450 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([CH2:12][CH:13]=[CH2:14])[CH2:9][NH:10][CH3:11])=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.[C:24]([C:26]1[CH:27]=[C:28]([C:36](Cl)=[O:37])[C:29]2[CH2:30][CH2:31][CH2:32][CH2:33][C:34]=2[CH:35]=1)#[N:25]>C(Cl)Cl>[C:24]([C:26]1[CH:27]=[C:28]([C:36]([N:10]([CH2:9][C@H:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)[CH2:12][CH:13]=[CH2:14])[CH3:11])=[O:37])[C:29]2[CH2:30][CH2:31][CH2:32][CH2:33][C:34]=2[CH:35]=1)#[N:25]

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 15536023[(2S)-2-(4-Fluorophenyl)pent-4-en-1-yl]methylamineHCID 224526673-Cyano-5,6,7,8-tetrahydronaphthalene-1-carbonyl chloride

生成物 1

HCID 689785133-cyano-N-[(2S)-2-(4-fluorophenyl)pent-4-en-1-yl]-N-methyl-5,6,7,8-tetrahydronaphthalene-1-carboxamide収率 78.8%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

[(2S)-2-(4-Fluorophenyl)pent-4-en-1-yl]methylamine (see Bioorg. Med. Chem. Lett; 2001; 265-270; 300 mg, 1.55 mmol) was dissolved in CH2Cl2 (30 m]L) and to the resultant solution were added DIPEA (440 mg, 3.40 mmol) together with 3-cyano-5,6,7,8-tetrahydronaphthalene-1-carbonyl chloride (see WO 00/34243; 341 mg, 1.55 mmol). The mixture was stirred for 2 h at room temperature, diluted with CH2Cl2 (20 mL) and then washed with water, aqueous KHSO4 solution and finally with brine. The solution was dried over Na2SO4 and then the solvent was evaporated. The residue was chromatographed on silica gel using a mixture of heptane and ethyl acetate as eluent (7:3) and there was obtained 460 mg (78%) of 3-cyano-N-[(2S)-2-(4-fluorophenyl)pent-4-en-1-yl]-N-methyl-5,6,7,8-tetrahydronaphthalene-1-carboxamide as an oil. 1H NMR (400 MHz, CDCl3): 0.8-4.2 (cm, 16H), 4.8-5.1 (m, 2H), 5.6-5.8 (m, 1H), 6.7-7.4 (cm, 6H); LCMS: m/z 377 (M+1)+.

後処理

  1. washwashed with water, aqueous KHSO4 solution and finally with brine
  2. dry with materialThe solution was dried over Na2SO4
  3. customthe solvent was evaporated
  4. customThe residue was chromatographed on silica gel using
  5. additiona mixture of heptane and ethyl acetate as eluent (7:3)

出典と根拠

ORDレコード
ord-82c5437a078b48b7a47678055bc0e6cb
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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