Triethylamine → 3-(4-Cyanophenyl)-N-{3-[(2,3-dichlorobenzenesulphonyl)methyl-amino]propyl}propionamide

HRID 1591748ノート

反応式

HRID 1591748 の反応式
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]([CH3:13])C(O)=O)=[CH:5][CH:4]=1)#[N:2].[CH3:14][N:15]([C:17]([O:21]N1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C([N:38]([CH2:41][CH3:42])[CH2:39]C)C.NCCCN(C)[S:48]([C:51]1[CH:56]=[CH:55][CH:54]=[C:53]([Cl:57])[C:52]=1[Cl:58])(=[O:50])=[O:49]>O1CCCC1>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH2:13][C:17]([NH:15][CH2:14][CH2:42][CH2:41][NH:38][CH2:39][S:48]([C:51]2[CH:56]=[CH:55][CH:54]=[C:53]([Cl:57])[C:52]=2[Cl:58])(=[O:49])=[O:50])=[O:21])=[CH:7][CH:8]=1)#[N:2]

参加物

6

反応物 4

HCID 8471TriethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 225698632-(4-Cyanophenyl)propanoic acidHCID 69423487N-(3-aminopropyl)-2,3-dichloro-N-methylbenzenesulphonamide

生成物 1

HCID 694217413-(4-Cyanophenyl)-N-{3-[(2,3-dichlorobenzenesulphonyl)methyl-amino]propyl}propionamide

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of 1.47 g (8.41 mmol) of 4-cyanophenylpropionic acid, 3.1 g (9.65 mmol) of TBTU and 5.0 ml of triethylamine in 150 ml of tetrahydrofuran was stirred at room temperature for 30 minutes, 2.5 g (8.41 mmol) of N-(3-aminopropyl)-2,3-dichloro-N-methylbenzenesulphonamide were than added and the mixture was stirred overnight. The mixture was evaporated to dryness, potassium carbonate solution (10%) was added to the residue and the mixture was extracted with ethyl acetate. The organic phase was washed with water and saturated sodium chloride solution, drive over sodium sulphate and concentrated. The crude product obtained in this manner was purified by column chromatography (mobile phase: dichloromethane/methanol 150:1 to 100:1).

後処理

  1. additionthan added
  2. customThe mixture was evaporated to dryness, potassium carbonate solution (10%)
  3. additionwas added to the residue
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic phase was washed with water and saturated sodium chloride solution, drive over sodium sulphate
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-3ef57e68456c4b97a671b3306a2a44c1
出典データセット
uspto-grants-2007_11
特許番号
US07291642B2

反応ノート

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