N,N-Dimethylethylenediamine → HCID 68918651, compound

HRID 1928887Notes

Reaction equation

HRID 1928887 reaction equation
Cl[CH2:2][C:3]([NH:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[N:12]=[C:11]([NH:16][CH:17]1[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][C:24]=3[O:26][CH3:27])[CH2:19][CH2:18]1)[CH:10]=[CH:9]2)=[O:4].[CH3:28][N:29]([CH3:33])[CH2:30][CH2:31][NH2:32]>C(=O)(O)[O-].[Na+]>[CH3:28][N:29]([CH3:33])[CH2:30][CH2:31][NH:32][CH2:2][C:3]([NH:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[N:12]=[C:11]([NH:16][CH:17]1[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][C:24]=3[O:26][CH3:27])[CH2:19][CH2:18]1)[CH:10]=[CH:9]2)=[O:4]

Participants

4

Reactant 2

HCID 66053N,N-DimethylethylenediamineHCID 57860966HCID 57860966, compound

Product 1

HCID 68918651HCID 68918651, compoundYield 88.1%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

rac-2-Chloro-N-[2-(7-methoxy-indan-1-ylamino)-quinolin-6-yl]-acetamide (150 mg, 0.39 mmol) was suspended N,N-dimethylethylendiamine (693 mg, 7.9 mmol) and placed in an ultrasound bath for 4 min. The mixture was diluted with 5 mL saturated sodium bicarbonate solution and was extracted three times with ethyl acetate and combined organic layers were dried over sodium sulfate. Removal of the solvent in vacuum left a yellow residue which was purified by silica gel column chromatography with dichloromethane/methanol to give the title compound as a white foam (149 mg, 87%). MS (ISN) m/e=432.5 [(M−H)−].

Workup

  1. extractionwas extracted three times with ethyl acetate
  2. dry with materialwere dried over sodium sulfate
  3. customRemoval of the solvent in vacuum
  4. waitleft a yellow residue which
  5. customwas purified by silica gel column chromatography with dichloromethane/methanol

Sources & evidence

ORD record
ord-9dbaa54cc05145edb8c4262d44e637d3
Source dataset
uspto-grants-2012_05
Patent number
US08183380B2

Reaction notes

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