Triethylamine → 1,5-dimethyl-1H-indole-4-carboxylic acid indan-2-yl-(4-methyl-benzyl)-amide

HRID 25274Notes

Reaction equation

HRID 25274 reaction equation
[CH3:1][CH2:2]N=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C.[CH3:29][N:30]1[C:38]2[CH:37]=[CH:36][C:35]([CH3:39])=[C:34]([C:40]([OH:42])=O)[C:33]=2[CH:32]=[CH:31]1.[C:43]1(C)[CH:48]=[CH:47][C:46]([NH:49][CH:50]2[CH2:58][C:57]3[C:52](=[CH:53][CH:54]=[CH:55][CH:56]=3)[CH2:51]2)=[CH:45][CH:44]=1>ClCCCl.ClCCl>[CH2:58]1[C:57]2[C:52](=[CH:53][CH:54]=[CH:55][CH:56]=2)[CH2:51][CH:50]1[N:49]([CH2:46][C:45]1[CH:44]=[CH:43][C:48]([CH3:47])=[CH:2][CH:1]=1)[C:40]([C:34]1[C:33]2[CH:32]=[CH:31][N:30]([CH3:29])[C:38]=2[CH:37]=[CH:36][C:35]=1[CH3:39])=[O:42]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 15637824HCID 15637824, compoundHCID 22566918HCID 22566918, compound

Product 1

HCID 207604451,5-dimethyl-1H-indole-4-carboxylic acid indan-2-yl-(4-methyl-benzyl)-amide

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

EDCI (2 equivalents), HOBT (1 equivalent), and 2.0 equivalents of triethylamine are added to a solution of 1,5-Dimethyl-1H-indole-4-carboxylic acid (23) (189 mg, 1.0 mmol) and (4-tolyl)-indan-2-ylamine (237 mg, 1.0 mmol, 1.0 eq.) (24) in 10 ml of anhydrous 1,2-dichloroethane. The resulting solution is stirred at room temperature for 5 hours and heated at reflux overnight. The reaction mixture is diluted with dichloromethane (20 ml), extracted with saturated sodium bicarbonate solution (10 ml×2), water (10 ml×2), and brine (10 ml). The organic layer is dried over anhydrous sodium sulfate, filtered and evaporated at reduced pressure, and purified by reverse-phase preparative HPLC to obtain 1,5-dimethyl-1H-indole-4-carboxylic acid indan-2-yl-(4-methyl-benzyl)-amide (25).

Workup

  1. temperatureheated
  2. temperatureat reflux overnight
  3. extractionextracted with saturated sodium bicarbonate solution (10 ml×2), water (10 ml×2), and brine (10 ml)
  4. dry with materialThe organic layer is dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customevaporated at reduced pressure
  7. custompurified by reverse-phase preparative HPLC

Sources & evidence

ORD record
ord-6f907081fd2247ff934af222ce80b6b0
Source dataset
uspto-grants-2005_02
Patent number
US06858637B2

Reaction notes

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