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

HRID 1392201Notes

Reaction equation

HRID 1392201 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-fa8416b59908466bbc8980e76f703b5f
Source dataset
uspto-grants-2008_03
Patent number
US07342029B2

Reaction notes

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