1-Naphthalenemethanamine → HCID 22988119, compound

HRID 987064Notes

Reaction equation

HRID 987064 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:11](C(O)=O)=[CH:10][CH:9]=[CH:8][N:7]=1)=[O:5])[CH3:2].[C:15]([N:22]1[CH:26]=[CH:25]N=C1)(N1C=CN=C1)=[O:16].NC[C:29]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36]C=2)[CH:32]=[CH:31][CH:30]=1>O1CCCC1.CN(C)C=O>[C:25]1([CH2:26][NH:22][C:15]([C:10]2[CH:9]=[CH:8][N:7]=[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH:11]=2)=[O:16])[C:38]2[C:33](=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:34]=[CH:35][CH:36]=1

Participants

5

Reactant 3

HCID 83551-NaphthalenemethanamineHCID 682631,1'-CarbonyldiimidazoleHCID 19154883HCID 19154883, compound

Product 1

HCID 22988119HCID 22988119, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 21974620tetrahydrofuran N,N-dimethylformamideSolvent

Procedure

4.9 g (25 mmol) of 2-ethoxycarbonylpyridine-3-carboxylic acid (N. Finch et al., J. Med. Chem. 1980, 23, 1405) were dissolved in 110 ml of tetrahydrofuran/dimethylformamide (10/1) and treated with 4.5 g (27.5 mmol) of 1,1′-carbonyldiimidazole. After the mixture had been stirred at room temperature for 30 min, 3.9 g (25 mmol) of 1-aminomethylnaphthalene were additionally added and the mixture was stirred at room temperature for a further 72 h. The tetrahydrofuran was then removed in vacuo and the residue was partitioned between 200 ml of ethyl acetate and 200 ml of aqueous sodium hydrogencarbonate solution. The organic phase was additionally washed with water, dried and concentrated in vacuo. 7.9 g (95%) of the product were obtained. 1H-NMR: [lacuna]

Workup

  1. stirringthe mixture was stirred at room temperature for a further 72 h
  2. customThe tetrahydrofuran was then removed in vacuo
  3. customthe residue was partitioned between 200 ml of ethyl acetate and 200 ml of aqueous sodium hydrogencarbonate solution
  4. washThe organic phase was additionally washed with water
  5. customdried
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8f827e986b9346f39e03f395deb7a582
Source dataset
uspto-grants-2003_10
Patent number
US06630493B1

Reaction notes

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