Triethylamine → HCID 59677014, compound

HRID 546509Notes

Reaction equation

HRID 546509 reaction equation
Cl.[CH3:2][O:3][CH:4]1[CH2:8][C@@H:7]([NH2:9])[C@H:6]([NH2:10])[CH2:5]1.C(N(CC)CC)C.[Cl:18][C:19]1[CH:20]=[C:21]2[C:25](=[CH:26][CH:27]=1)[NH:24][C:23]([C:28](OC1C=CC([N+]([O-])=O)=CC=1)=[O:29])=[CH:22]2>CN(C)C=O>[CH3:2][O:3][CH:4]1[CH2:8][C@@H:7]([NH:9][C:28]([C:23]2[NH:24][C:25]3[C:21]([CH:22]=2)=[CH:20][C:19]([Cl:18])=[CH:27][CH:26]=3)=[O:29])[C@H:6]([NH2:10])[CH2:5]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 178424154-Nitrophenyl 5-chloro-1H-indole-2-carboxylateHCID 57481677HCID 57481677, compound

Product 1

HCID 59677014HCID 59677014, compoundYield 34.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(1R*,2R*)-4-Methoxy-1,2-cyclopentanediamine hydrochloride (470 mg) was suspended in N,N-dimethylformamide (5 ml), and triethylamine (0.966 ml) and p-nitrophenyl 5-chloroindole-2-carboxylate (805 mg) were added to stir the mixture at room temperature for 4 days. The solvent was distilled off under reduced pressure, and a saturated aqueous solution of sodium hydrogencarbonate and dichloromethane were added to the residue to conduct liquid separation. The resultant organic layers 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 (1R*,2R*)-4-methoxy-N1-[(5-chloroindol-2-yl)carbonyl]-1,2-cyclopentanediamine (mixture of stereoisomers at 4-position) (268 mg) as yellow powder.

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. additiona saturated aqueous solution of sodium hydrogencarbonate and dichloromethane were added to the residue
  3. customliquid separation
  4. dry with materialThe resultant organic layers 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-4199362da5c744248fc8045c36bac3c0
Source dataset
uspto-grants-2011_05
Patent number
US07935824B2

Reaction notes

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