HCID 19093752, compound → HCID 19093708, compound

HRID 1587523Notes

Reaction equation

HRID 1587523 reaction equation
C([NH:5][S:6]([C:9]1[C:10]([C:15]2[CH:20]=[CH:19][C:18]([CH2:21][N:22]3[C:31]4[C:26](=[C:27]([CH2:34][CH3:35])[N:28]=[C:29]([CH2:32][CH3:33])[CH:30]=4)[CH:25]=[CH:24][C:23]3=[O:36])=[CH:17][CH:16]=2)=[CH:11][CH:12]=[CH:13][CH:14]=1)(=[O:8])=[O:7])(C)(C)C>FC(F)(F)C(O)=O>[CH2:34]([C:27]1[N:28]=[C:29]([CH2:32][CH3:33])[CH:30]=[C:31]2[C:26]=1[CH:25]=[CH:24][C:23](=[O:36])[N:22]2[CH2:21][C:18]1[CH:19]=[CH:20][C:15]([C:10]2[C:9]([S:6]([NH2:5])(=[O:7])=[O:8])=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:16][CH:17]=1)[CH3:35]

Participants

3

Reactant 1

HCID 19093752HCID 19093752, compound

Product 1

HCID 19093708HCID 19093708, compoundYield 77.1%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of N-tert-butyl-4'-[(5,7-diethyl-2-oxo-1,2-dihydro-1,6-naphthyridin-1-yl)methyl]biphenyl-2-sulphonamide (200 mg) in trifluoroacetic acid (5 ml) was heated at reflux for 3 hours. Volatile material was removed by evaporation and water was added to the residue. The resultant solution was basified by the addition of solid potassium carbonate and then extracted twice with ethyl acetate. The combined extracts were washed with water, saturated sodium chloride solution and then dried (MgSO4). The solvent was removed by evaporation to give 4'-[(5,7-diethyl-2-oxo-1,2-dihydro-1,6-naphthyridin-1-yl)methyl]biphenyl-2-sulphonamide as a solid (137 mg); m.p. 199°-200° C.; NMR (d6 -DMSO): 1.18(t, 3H), 1.26(t, 3H), 2.73(q, 2H), 3.07(q, 2H), 5.54(s, 2H), 6.72(d, 1H), 7.1-7.7(m, 10H), 8.01(dd, 1H), 8.23(d, 1H); mass spectrum (+ve FAB, methanol/NBA): 448 (M+H)+ ; microanalysis, found: C, 67.0; H, 5.5; N, 9.2%; C25H25N3O3S requires: C, 67.1; H, 5.6; N, 9.4%.

Workup

  1. temperatureat reflux for 3 hours
  2. customVolatile material was removed by evaporation and water
  3. additionwas added to the residue
  4. additionThe resultant solution was basified by the addition of solid potassium carbonate
  5. extractionextracted twice with ethyl acetate
  6. washThe combined extracts were washed with water, saturated sodium chloride solution
  7. dry with materialdried (MgSO4)
  8. customThe solvent was removed by evaporation

Sources & evidence

ORD record
ord-c6e4fffe261c45eea1010a1dafe50bc5
Source dataset
uspto-grants-1993_06
Patent number
US05217976

Reaction notes

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