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

HRID 1392201노트

반응식

HRID 1392201 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-fa8416b59908466bbc8980e76f703b5f
출처 데이터셋
uspto-grants-2008_03
특허 번호
US07342029B2

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