Triethylamine → HCID 68909747, compound

HRID 459597Notes

Reaction equation

HRID 459597 reaction equation
Cl.[CH3:2][O:3][C@H:4]1[C@@H:9]([O:10][CH3:11])[CH2:8][C@@H:7]([NH2:12])[C@@H:6]([NH2:13])[CH2:5]1.Cl.CO[C@@H]1[C@H](OC)C[C@@H](N)[C@@H](N)C1.C(N(CC)CC)C.[Cl:34][C:35]1[CH:36]=[C:37]2[C:41](=[CH:42][CH:43]=1)[NH:40][C:39]([C:44](OC1C=CC([N+]([O-])=O)=CC=1)=[O:45])=[CH:38]2>CN(C)C=O>[Cl:34][C:35]1[CH:36]=[C:37]2[C:41](=[CH:42][CH:43]=1)[NH:40][C:39]([C:44]([NH:12][C@@H:7]1[CH2:8][C@H:9]([O:10][CH3:11])[C@H:4]([O:3][CH3:2])[CH2:5][C@@H:6]1[NH2:13])=[O:45])=[CH:38]2

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 178424154-Nitrophenyl 5-chloro-1H-indole-2-carboxylateHCID 68907936HCID 68907936, compoundHCID 68909445HCID 68909445, compound

Product 1

HCID 68909747HCID 68909747, compoundYield 32.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture (645 mg) of (1R*,2S*,4R*,5S*)-4,5-dimethoxy-1,2-cyclohexanediamine hydrochloride and (1R*,2S*,4S*,5R*)-4,5-dimethoxy-1,2-cyclohexanediamine hydrochloride was suspended in N,N-dimethylformamide (50 ml), and triethylamine (1.10 ml) and p-nitrophenyl 5-chloroindole-2-carboxylate (920 mg) were added to stir the mixture overnight at room temperature. The reaction mixture was concentrated under reduced pressure, and a saturated aqueous solution of sodium hydrogencarbonate was added to the residue to conduct extraction with dichloromethane. The resultant organic layer was dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by column chromatography on silica gel (methanol:dichloromethane=1:9) to obtain a mixture (330 mg) of (1R*,2S*,4R*,5S*)-N1-[(5-chloroindol-2-yl)carbonyl]-4,5-dimethoxy-1,2-cyclohexanediamine and (1R*,2S*,4S*,5R*)-N1-[(5-chloroindol-2-yl)carbonyl]-4,5-dimethoxy-1,2-cyclohexanediamine as pale yellow powder.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additiona saturated aqueous solution of sodium hydrogencarbonate was added to the residue
  3. extractionextraction with dichloromethane
  4. dry with materialThe resultant organic layer was dried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe residue was purified by column chromatography on silica gel (methanol:dichloromethane=1:9)

Sources & evidence

ORD record
ord-ab8290c3c0954aa8a5abe081b0a6d10c
Source dataset
uspto-grants-2007_03
Patent number
US07192968B2

Reaction notes

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