1,1'-Carbonyldiimidazole → HCID 90002406, compound

HRID 587852Notes

Reaction equation

HRID 587852 reaction equation
[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH:4]([C:12]([OH:14])=O)[CH2:3]1.C1N=CN(C(N2C=NC=C2)=O)C=1.[C:27]1([C@H:37]([NH2:39])[CH3:38])[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH:30]=[CH:29][CH:28]=1>CN(C=O)C>[C:27]1([C@H:37]([NH:39][C:12]([CH:4]2[CH2:3][C:2](=[O:1])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[CH2:5]2)=[O:14])[CH3:38])[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH:30]=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 2229644-Oxo-1,2,3,4-tetrahydronaphthalene-2-carboxylic acidHCID 2724264(+)-1-(1-Naphthyl)ethylamine

Product 1

HCID 90002406HCID 90002406, compoundYield 96.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 4-oxo-1,2,3,4-tetrahydronaphthalene-2-carboxylic acid (4.6 g, 24.19 mmol) (Tetrahedron: Asymmetry 14, 2003, 3689; Journal of Medicinal Chemistry 25, 1982, 535), in DMF (20 mL), CDI (3.92 g, 24.19 mmol) was added. The reaction mixture was stirred at room temperature (RT) for 2 h. Then (R)-1-(naphthalen-1-yl)ethanamine (5.40 g, 31.5 mmol) was added and the reaction mixture was stirred at RT overnight. After completion of reaction, ice was added to the reaction mixture, solid precipitated out was filtered on Buchner funnel, washed with DM water (50 mL) and dried to get crude compound. Compound was further purified by flash chromatography (biotage) using eluent 15% ethyl acetate:hexane to yield the title compound (8 g, 96%); m/z 344.

Workup

  1. stirringthe reaction mixture was stirred at RT overnight
  2. customAfter completion of reaction, ice
  3. additionwas added to the reaction mixture, solid
  4. customprecipitated out
  5. filtrationwas filtered on Buchner funnel
  6. washwashed with DM water (50 mL)
  7. customdried
  8. customto get crude compound
  9. customCompound was further purified by flash chromatography (biotage)

Sources & evidence

ORD record
ord-5fd7bde9fe2e4578b4f6858c4140846b
Source dataset
uspto-grants-2016_01
Patent number
US09227919B2

Reaction notes

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