4-Methylmorpholine → Ethyl 2-[3-(5,6,7,8-tetrahydro-[1,8]naphthyridin-2-yl)-propylcarbamoyl]-acetate

HRID 617903Notes

Reaction equation

HRID 617903 reaction equation
[N:1]1[C:10]2[NH:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][C:2]=1[CH2:11][CH2:12][CH2:13][NH2:14].C([CH:17]([C:21]([OH:23])=O)[C:18]([OH:20])=[O:19])C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)[C:35]2C=CC=C[C:34]=2N=N1.CN1CCOCC1>CN(C=O)C.C(OCC)(=O)C>[N:1]1[C:10]2[NH:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][C:2]=1[CH2:11][CH2:12][CH2:13][NH:14][C:21]([CH2:17][C:18]([O:20][CH2:34][CH3:35])=[O:19])=[O:23]

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 11756Ethylmalonic acidHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 98775993-(5,6,7,8-Tetrahydro-1,8-naphthyridin-2-yl)propan-1-amine

Product 1

HCID 21850003Ethyl 2-[3-(5,6,7,8-tetrahydro-[1,8]naphthyridin-2-yl)-propylcarbamoyl]-acetate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1-8 (0.068 g, 0.36 mmol), ethylmalonic acid (0.052 g, 0.40 mmol), BOP (0.24 g, 0.54 mmol), and NMM (0.16 mL, 1.4 mmol) in DMF (1.8 mL) was stirred at ambient temperature for 20 h. The mixture was diluted with ethyl acetate, washed with water, brine, and dried over MgSO4. Following evaporative removal of the solvent, the residue was chromatographed on silica gel, eluting with 15% ethanol/EtOAc to give 1-9 as a colorless glass.

Workup

  1. washwashed with water, brine
  2. dry with materialdried over MgSO4
  3. customremoval of the solvent
  4. customthe residue was chromatographed on silica gel
  5. washeluting with 15% ethanol/EtOAc

Sources & evidence

ORD record
ord-532b10e154474506ac8549ea4b856d4a
Source dataset
uspto-grants-1999_09
Patent number
US05952341

Reaction notes

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