Water → HCID 19093748, compound

HRID 487401Notes

Reaction equation

HRID 487401 reaction equation
[H-].[Na+].[C:3]1([SH:9])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl[C:11]1[C:20]2[C:15](=[CH:16][C:17]([CH2:23][CH3:24])=[N:18][C:19]=2[CH2:21][CH3:22])[N:14]([CH2:25][C:26]2[CH:31]=[CH:30][C:29]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=3[C:38]3[N:39]=[N:40][N:41]([C:43]([C:56]4[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=4)([C:50]4[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=4)[C:44]4[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=4)[N:42]=3)=[CH:28][CH:27]=2)[C:13](=[O:62])[CH:12]=1.O>CC(N(C)C)=O>[CH2:21]([C:19]1[N:18]=[C:17]([CH2:23][CH3:24])[CH:16]=[C:15]2[C:20]=1[C:11]([S:9][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)=[CH:12][C:13](=[O:62])[N:14]2[CH2:25][C:26]1[CH:27]=[CH:28][C:29]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=2[C:38]2[N:39]=[N:40][N:41]([C:43]([C:56]3[CH:57]=[CH:58][CH:59]=[CH:60][CH:61]=3)([C:50]3[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=3)[C:44]3[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=3)[N:42]=2)=[CH:30][CH:31]=1)[CH3:22]

Participants

6

Reactant 4

HCID 962WaterHCID 7969ThiophenolHCID 24758Sodium hydrideHCID 19093663HCID 19093663, compound

Product 1

HCID 19093748HCID 19093748, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

Sodium hydride (50% dispersion in oil; 100 mg) was added to a stirred solution of thiophenol (0.2 ml) in dimethylacetamide (10 ml) and the mixture was stirred until effervescence ceased. 4-Chloro-5,7-diethyl-1-[(2'-(2-triphenylmethyl-2H-tetrazol-5-yl)biphenyl-4-yl)methyl]-1,6-naphthyridin-2(1H)-one (0.7 g) was added to the solution and the mixture was stirred at 50° C. for 4 hours. The reaction mixture was then poured into water and extracted twice with ethyl acetate. The combined extracts were washed with water, saturated sodium chloride solution and dried (MgSO4). Solvent was removed by evaporation to leave an oil which was purified by flash chromatography, eluting with ethyl acetate/petroleum ether (3:1 v/v, increasing to 2:5 v/v) to give 5,7-diethyl-4-phenylthio-1-[(2'-(2-triphenylmethyl-2H-tetrazol-5-yl)biphenyl-4yl)methyl[-1,6-naphthyridin-2(1H)-one (A) as a solid (0.53 g); m.p. 166°-168° C. (after recrystallisation from acetonitrile); NMR (d6 -DMSO): 1.07(t, 3H), 1.40(t, 3H), 2.58(q, 2H), 3.47(q, 2H), 5.40(s, 2H), 5.80(s, 1H), 6.8-7.8(complex m, 29H); mass spectrum (+ve FAB): 787 (M+H)+ ; microanalysis, found: C, 78.1; H, 5.1; N, 10.9%; C51H42N6OS requires: C, 77.8; H, 5.4; N, 10.7%.

Workup

  1. stirringthe mixture was stirred at 50° C. for 4 hours
  2. extractionextracted twice with ethyl acetate
  3. washThe combined extracts were washed with water, saturated sodium chloride solution
  4. dry with materialdried (MgSO4)
  5. customSolvent was removed by evaporation
  6. customto leave an oil which
  7. customwas purified by flash chromatography
  8. washeluting with ethyl acetate/petroleum ether (3:1 v/v, increasing to 2:5 v/v)

Sources & evidence

ORD record
ord-7a25a5971b304e468b20bd6322629b6c
Source dataset
uspto-grants-1994_03
Patent number
US05294620

Reaction notes

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