1,2-Dichloroethane → 3-(5-5,6,7,8-Tetrahydro-[1,8]naphthyridin-2-yl-pentanoylamino)-propionic acid

HRID 1837899Notes

Reaction equation

HRID 1837899 reaction equation
Cl.[N:2]1[C:11]2[NH:10][CH2:9][CH2:8][CH2:7][C:6]=2[CH:5]=[CH:4][C:3]=1[CH2:12][CH2:13][CH2:14][CH2:15][C:16]([OH:18])=O.C(Cl)CCl.C1C=CC2N([OH:32])N=NC=2C=1.C[N:34]1[CH2:39][CH2:38]OCC1.CN([CH:43]=[O:44])C>C(OCC)(=O)C>[N:2]1[C:11]2[NH:10][CH2:9][CH2:8][CH2:7][C:6]=2[CH:5]=[CH:4][C:3]=1[CH2:12][CH2:13][CH2:14][CH2:15][C:16]([NH:34][CH2:39][CH2:38][C:43]([OH:44])=[O:32])=[O:18]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 6228DimethylformamideHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 697750595-(5,6,7,8-Tetrahydro-1,8-naphthyridin-2-yl)pentanoic acid hydrochloride

Product 1

HCID 99011043-(5-5,6,7,8-Tetrahydro-[1,8]naphthyridin-2-yl-pentanoylamino)-propionic acid

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of acid 1-6 (10.8 mg, 0.04 mmol), EDC (7.7 mg, 0.04 mmol), HOBT (5.4 mg, 0.04 mmol) and NMM (0.026 mL, 0.24 mmol) in DMF (1 mL) was agitated until clear solution. After 30 minutes, amine 12-1 was added. The solution was agitated for one minute and then let stand for 18 h. The solution was diluted with ethyl acetate, washed with sat. NaHCO3 and H2O. Following evaporative removal of the solvent, the residue was dissolved in 90:10 TFA/H2O (1 ml). After 2 h, the solvents were evaporated to give acid 12-2.

Workup

  1. stirringThe solution was agitated for one minute
  2. waitlet stand for 18 h
  3. washwashed with sat. NaHCO3 and H2O
  4. customremoval of the solvent
  5. dissolutionthe residue was dissolved in 90:10 TFA/H2O (1 ml)
  6. waitAfter 2 h
  7. customthe solvents were evaporated

Sources & evidence

ORD record
ord-4abd890d8ead460dae98a8df4c6230a2
Source dataset
uspto-grants-2004_08
Patent number
US06784190B2

Reaction notes

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