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Triethylamine → N-[3-(3-chloro-5-cyano-2-methyl-1H-pyrrol-1-yl)-1-methylpropyl]-2-cyano-3,4,4-trimethylpentanamide

HRID 720776
ノート
印刷プレビュー

反応式

HRID 720776 の反応式
[C:1]([CH:3]([CH:7]([CH3:12])[C:8]([CH3:11])([CH3:10])[CH3:9])[C:4]([OH:6])=O)#[N:2].[NH2:13][CH:14]([CH3:26])[CH2:15][CH2:16][N:17]1[C:21]([CH3:22])=[C:20]([Cl:23])[CH:19]=[C:18]1[C:24]#[N:25].C(N(CC)CC)C>S(Cl)(Cl)=O.C(OCC)(=O)C>[Cl:23][C:20]1[CH:19]=[C:18]([C:24]#[N:25])[N:17]([CH2:16][CH2:15][CH:14]([NH:13][C:4](=[O:6])[CH:3]([C:1]#[N:2])[CH:7]([CH3:12])[C:8]([CH3:11])([CH3:10])[CH3:9])[CH3:26])[C:21]=1[CH3:22]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 8471TriethylamineHCID 218952532-Cyano-3,4,4-trimethylpentanoic acidHCID 218952681-(3-aminobutyl)-4-chloro-5-methyl-1H-pyrrole-2-carbonitrile

生成物 1

HCID 21895244N-[3-(3-chloro-5-cyano-2-methyl-1H-pyrrol-1-yl)-1-methylpropyl]-2-cyano-3,4,4-trimethylpentanamide

試薬・触媒・溶媒 2

HCID 8857Ethyl Acetate溶媒
HCID 24386
Thionyl Chloride
溶媒
2 回

実験手順

A solution of 0.54 g (3.5 mmol) 2-cyano-3,4,4-trimethylpentanoic acid in 15 mL thionyl chloride was heated at reflux for 30 min. The thionyl chloride was stripped and the residue was dried in vacuo. The residue was then dissolved in 20 mL methylene chloride and a solution of 0.66 g (3.13 mmol) of 1-(3-aminobutyl)-4-chloro-5-methyl-1H-pyrrole-2-carbonitrile and 0.59 mL (4.2 mmol) triethylamine was added dropwise. The mixture was stirred at room temperature overnight. Solvent was stripped and the residue was taken up in ethyl acetate which was washed with water and brine. Drying (MgSO4) and removal of solvent gave an oil which was chromatographed (40% ether in hexanes) on silica gel to give the title compound as a mixture of diastereomers, mp 111–118° C. 1H NMR (CDCl3) δ 1.0 (m, 3H), 1.2–1.3 (2m, 6H), 1.4 (d, 1H), 1.6 (m, 2H), 1.9 (m, 2H), 2.2 (m, 3H), 4.1 (2m, 2H), 5.7 (m, 1H), 6.65 (2s, 1H).

後処理

  1. temperatureat reflux for 30 min
  2. customthe residue was dried in vacuo
  3. dissolutionThe residue was then dissolved in 20 mL methylene chloride
  4. washwas washed with water and brine
  5. customDrying
  6. custom(MgSO4) and removal of solvent
  7. customgave an oil which
  8. customwas chromatographed (40% ether in hexanes) on silica gel

出典と根拠

ORDレコード
ord-ff5eaa747ed84a6ab5ad0e08fe7251bb
出典データセット
uspto-grants-2006_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07135585B2

反応ノート

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