Diethyl Ether → HCID 19756360, compound

HRID 1587833Notes

Reaction equation

HRID 1587833 reaction equation
[H-].[Na+].[CH2:3]([C:5]1[CH:14]=[C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[C:29]3[N:30]=[N:31][N:32]([C:34]([C:47]4[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=4)([C:41]4[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=4)[C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)[N:33]=3)=[CH:19][CH:18]=2)[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:53][CH2:54][CH2:55][OH:56])[N:11]=2)[N:6]=1)[CH3:4].[H][H].[CH3:59][CH2:60][O:61]CC>C1COCC1>[CH2:3]([C:5]1[CH:14]=[C:13]([O:15][CH2:16][C:17]2[CH:18]=[CH:19][C:20]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[C:29]3[N:30]=[N:31][N:32]([C:34]([C:47]4[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=4)([C:41]4[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=4)[C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)[N:33]=3)=[CH:21][CH:22]=2)[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:53][CH2:54][C:55]([O:61][CH2:60][CH3:59])=[O:56])[N:11]=2)[N:6]=1)[CH3:4]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 24758Sodium hydrideHCID 19756350HCID 19756350, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19756360HCID 19756360, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Sodium hydride (60% dispersion in mineral oil, 62 mg) was added to a solution of 2-ethyl-6-(2-hydroxyethoxy)-4-[(2'-(2-triphenylmethyl-2H-tetrazol-5-yl)biphenyl-4-yl)methoxy]-1,5-naphthyridine (1.0 g) in THF (10 ml). The mixture was stirred until evolution of hydrogen had ceased and then 1-(4-morpholinocarbonyl)imidazole (285 mg) in THF (10 ml) was added. The solution was heated under reflux for 3 hours and then cooled. Ether (50 ml) was added and the solution was washed with water (2×30 ml) and dried (MgSO4). Volatile material was removed by evaporation an the residue was recrystallised from a mixture of ether and hexane to give 2-ethyl-6-[2-(4-morpholinocarbonyloxy)ethoxy]-4-[(2'-(2-triphenylmethyl-2H-tetrazol-5-yl)biphenyl-4-yl)methoxy]-1,5-naphthyridine (A) (0.82 g), m.p. 76°-79° C.; NMR (d6 -DMSO): 1.3(t, 3H), 2.85(q, 2H), 3.2-3.3(m, 4H), 3.3-3.5(m, 4H), 4.3-4.4(m, 2H), 4.6-4.7(m, 2H), 5.35(s, 2H), 6.8-6.9(m, 6H), 7.1-7.7(complex m, 18H), 7.8(dd, 1H), 8.15(d, 1H),

Workup

  1. temperatureThe solution was heated
  2. temperatureunder reflux for 3 hours
  3. temperaturecooled
  4. washthe solution was washed with water (2×30 ml)
  5. dry with materialdried (MgSO4)
  6. customVolatile material was removed by evaporation an the residue
  7. customwas recrystallised from a mixture of ether and hexane

Sources & evidence

ORD record
ord-e7ed20e3963a49bfb99220ab025db7c8
Source dataset
uspto-grants-1993_06
Patent number
US05219863

Reaction notes

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