1-Pyrrolidineethanamine → HCID 18508358, compound

HRID 1356466Notes

Reaction equation

HRID 1356466 reaction equation
[NH2:1][CH2:2][CH2:3][N:4]1[CH2:8][CH2:7][CH2:6][CH2:5]1.[C:9]1([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:14]=[CH:13][C:12]([CH2:15][N:16]2[C:21](=[O:22])[CH:20]=[CH:19][C:18]([C:23](O)=[O:24])=[CH:17]2)=[CH:11][CH:10]=1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>C(#N)C.C(=O)([O-])[O-].[K+].[K+].C(N(CC)CC)C.C1COCC1>[C:9]1([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:10]=[CH:11][C:12]([CH2:15][N:16]2[C:21](=[O:22])[CH:20]=[CH:19][C:18]([C:23]([NH:1][CH2:2][CH2:3][N:4]3[CH2:8][CH2:7][CH2:6][CH2:5]3)=[O:24])=[CH:17]2)=[CH:13][CH:14]=1

Participants

9

Reactant 4

HCID 13441-PyrrolidineethanamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 17817484HCID 17817484, compound

Product 1

HCID 18508358HCID 18508358, compoundYield 68.4%

Reagents, catalysts & solvents 4

HCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolventHCID 11430Potassium CarbonateSolvent

Procedure

To a solution of 1-(2-aminoethyl)pyrrolidine (230 mg) in acetonitrile (5 ml)/THF (10 ml) were added 1-(4-biphenylylmethyl)-1,6-dihydro-6-oxo-3-pyridinecarboxylic acid (500 mg), WSC (380 mg), HOBt (260 mg), and triethylamine (0.7 ml) at room temperature. After stirring at room temperature for 12 hr, the reaction mixture was diluted with 5% aqueous potassium carbonate and extracted with ethyl acetate. The organic layer was washed with water and saturated aqueous sodium chloride sequentially, dried, and the solvent was removed in vacuo. The residue was purified by alumina column chromatography (eluent; THF) and recrystallized from ethyl acetate/diisopropylether to obtain the titled compound (450 mg).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated aqueous sodium chloride sequentially
  3. customdried
  4. customthe solvent was removed in vacuo
  5. customThe residue was purified by alumina column chromatography (eluent; THF)
  6. customrecrystallized from ethyl acetate/diisopropylether

Sources & evidence

ORD record
ord-0b42fd7ba82548959beee945c9136e05
Source dataset
uspto-grants-2003_07
Patent number
US06586475B1

Reaction notes

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