Diisopropylamine → N-(1-Carbamoyl-3-phenylpropyl)-2,3-diphenyl-1H-indole-5-carboxamide

HRID 1392201ノート

反応式

HRID 1392201 の反応式
[C:1]1([C:7]2[NH:8][C:9]3[C:14]([C:15]=2[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:13][C:12]([C:22](O)=[O:23])=[CH:11][CH:10]=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[NH2:26][C@H:27]([C:36]([NH2:38])=[O:37])[CH2:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C(NC(C)C)(C)C>CN(C)C=O>[C:36]([CH:27]([NH:26][C:22]([C:12]1[CH:13]=[C:14]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)=[C:15]2[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:23])[CH2:28][CH2:29][C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)(=[O:37])[NH2:38]

参加物

5

反応物 3

HCID 7912DiisopropylamineHCID 39003082,3-diphenyl-1H-indole-5-carboxylic AcidHCID 18685852L-homophenylalaninamide hydrochloride

生成物 1

HCID 15521532N-(1-Carbamoyl-3-phenylpropyl)-2,3-diphenyl-1H-indole-5-carboxamide

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

0.16 g (0.5 mmol) of 2,3-diphenyl-1H-indole-5-carboxylic acid (see process variant A) was dissolved at RT in 10 ml of dry dimethylformamide (DMF) and admixed successively with 0.11 g (0.5 mmol) of L-homophenyl-alaninamide hydrochloride, 0.16 g of TOTU (O-[(cyano(ethoxycarbonyl)-methylidene)amino-1,1,3,3-tetramethyl]uronium tetrafluoroborate) and 0.14 ml (1 mmol) of diisopropylamine. The reaction mixture was stirred at RT for 6 h and then concentrated under reduced pressure, and the residue was dissolved in ethyl acetate. The organic phase was washed successively with water, saturated sodium carbonate solution, water and saturated sodium chloride solution, dried over magnesium sulfate, filtered and concentrated under reduced pressure. This gave N-(1-carbamoyl-3-phenylpropyl)-2,3-diphenyl-1H-indole-5-carboxamide of melting point 120° C. to 125° C.

後処理

  1. concentrationconcentrated under reduced pressure
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washThe organic phase was washed successively with water, saturated sodium carbonate solution, water and saturated sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-fa8416b59908466bbc8980e76f703b5f
出典データセット
uspto-grants-2008_03
特許番号
US07342029B2

反応ノート

読み込み中…