Diisopropylethylamine → N-(2-(5-Chloro-1H-indol-3-yl)ethyl)-4-(phenylamino)benzamide

HRID 1777695ノート

反応式

HRID 1777695 の反応式
C[N:2]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=O)=[CH:5][CH:4]=1.Cl.[Cl:19][C:20]1[CH:21]=[C:22]2[C:26](=[CH:27][CH:28]=1)[NH:25][CH:24]=[C:23]2[CH2:29][CH2:30][NH2:31].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C>CN(C=O)C>[Cl:19][C:20]1[CH:21]=[C:22]2[C:26](=[CH:27][CH:28]=1)[NH:25][CH:24]=[C:23]2[CH2:29][CH2:30][NH:31][C:7](=[O:9])[C:6]1[CH:5]=[CH:4][C:3]([NH:2][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[CH:11][CH:10]=1

参加物

6

反応物 4

HCID 81531DiisopropylethylamineHCID 28274945-Chloro-1H-indole-3-ethylamine monohydrochlorideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 232051694-(Methyl(phenyl)amino)benzoic acid

生成物 1

HCID 67974945N-(2-(5-Chloro-1H-indol-3-yl)ethyl)-4-(phenylamino)benzamide収率 14.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A solution of 4-(methyl(phenyl)amino)benzoic acid (0.045 g, 0.198 mmol), 2-(5-chloro-1H-indol-3-yl)ethanamine hydrochloride (0.046 g; 0.198 mmol), HATU (0.083 g; 0.217 mmol) and N,N-diisoproylethylamine (0.085 mL; 0.495 mmol) in DMF (3 mL), was stirred at room temperature overnight. The reaction mixture was partitioned between ethyl acetate and sodium hydrogen sulphate, the organic layer was washed with sodium carbonate, brine, dried and concentrated in vacuo. The crude mixture was purified by flash chromatography on silica (eluent 20 to 100% ethyl acetate in heptane) to yield 0.011 g (14%) of the title compound as a white solid.

後処理

  1. customThe reaction mixture was partitioned between ethyl acetate and sodium hydrogen sulphate
  2. washthe organic layer was washed with sodium carbonate, brine
  3. customdried
  4. concentrationconcentrated in vacuo
  5. customThe crude mixture was purified by flash chromatography on silica (eluent 20 to 100% ethyl acetate in heptane)

出典と根拠

ORDレコード
ord-2ef3f07281a248c58b7de332e51cb3a0
出典データセット
uspto-grants-2016_02
特許番号
US09266832B2

反応ノート

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