Ammonium Chloride → HCID 59831665, compound

HRID 1716638Notes

Reaction equation

HRID 1716638 reaction equation
[CH3:1][NH2:2].Cl.[CH3:4][Al](C)C.C([O:10][C:11](=O)[CH2:12][CH:13]([C:23]1[CH:31]=[C:30]2[C:26]([CH:27]=CN2)=[CH:25][CH:24]=1)[C:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[NH:16][CH:15]=1)C.[NH4+:33].[Cl-]>C1C=CC=CC=1>[NH:2]1[C:30]2[C:26](=[CH:25][CH:24]=[C:23]([CH:13]([C:14]3[C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[NH:16][CH:15]=3)[CH2:12][C:11]([NH:33][CH3:4])=[O:10])[CH:31]=2)[CH:27]=[CH:1]1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 6364545Methylamine hydrochlorideHCID 16682925TrimethylaluminumHCID 598316643-(1H-Indol-6-yl)-3-(1H-indol-3-yl)-propionic acid ethyl ester

Product 1

HCID 59831665HCID 59831665, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

To a 0° C. suspension of MeNH2—HCl (97.9 mg, 1.45 mmol) in benzene (4 ml) was added Me3Al (2 M in toluene, 746 μl, 1.45 mmol). The mixture was stirred for 5 minutes and at room temperature for about 1.25 hours. A suspension of 3-(1H-indol-6-yl)-3-(1H-indol-3-yl)-propionic acid ethyl ester XXVII in benzene (15 ml) was added, and the resulting reaction mixture was stirred at reflux for 8 hours, and at room temperature for 16 hours. The reaction mixture was diluted with a saturated solution of NH4Cl (20 ml) and extracted with EtOAc. The organic layers were combined, dried over Na2SO4, filtered, concentrated, and purified via flash chromatography (DCM/MeOH) affording 3-(1H-Indol-6-yl)-3-(1H-indol-3-yl)-N-methyl-propionamide XXVIII as a yellow oil (86 mg).

Workup

  1. additionwas added
  2. customthe resulting reaction mixture
  3. stirringwas stirred
  4. temperatureat reflux for 8 hours
  5. waitat room temperature for 16 hours
  6. extractionextracted with EtOAc
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. custompurified via flash chromatography (DCM/MeOH)

Sources & evidence

ORD record
ord-5f3018e52d6b4b158cf190492f82438c
Source dataset
uspto-grants-2010_09
Patent number
US07803830B2

Reaction notes

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