Water → HCID 19756360, compound

HRID 1587837Notes

Reaction equation

HRID 1587837 reaction equation
[CH2:1]([O:3][C:4]([CH:6]([O:8][C:9]1[N:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[N:15]=[C:14]([CH2:19][CH3:20])[CH:13]=[C:12]2[O:21][CH2:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[C:35]2[N:36]=[N:37][N:38]([C:40]([C:53]3[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=3)([C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=3)[C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[N:39]=2)=[CH:25][CH:24]=1)C)=[O:5])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>C1COCC1>[CH2:19]([C:14]1[CH:13]=[C:12]([O:21][CH2:22][C:23]2[CH:24]=[CH:25][C:26]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[C:35]3[N:36]=[N:37][N:38]([C:40]([C:53]4[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=4)([C:47]4[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=4)[C:41]4[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=4)[N:39]=3)=[CH:27][CH:28]=2)[C:11]2[C:16](=[CH:17][CH:18]=[C:9]([O:8][CH2:6][C:4]([O:3][CH2:1][CH3:2])=[O:5])[N:10]=2)[N:15]=1)[CH3:20]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 19756353HCID 19756353, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 19756360HCID 19756360, compoundYield 90.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 6-[1-(ethoxycarbonyl)ethoxy]-2-ethyl-4-[(2'-(2-triphenylmethyl-2H-tetrazol-5-yl)biphenyl-4-yl)methoxy]-1,5-naphthyridine (1.0 g) in THF (8 ml) was added to a stirred suspension of lithium aluminium hydride (100 mg) in THF (5 ml) at 0° C. The mixture was allowed to warm to ambient temperature and then stirred for 20 hours. Water (0.1 ml), 15% w/v sodium hydroxide solution (0.1 ml) and water (0.3 ml) were added and the mixture was stirred for 30 minutes. The insoluble solid was removed by filtration and the filtrate was concentrated by evaporation. The residue was triturated with ether to give 2-ethyl-6-(1-hydroxy-2-propoxy)-4-[(2'-(2-triphenylmethyl-2H-tetrazol-5-yl)biphenyl-4-yl)methoxy]-1,5-naphthyridine (A) (0.89 g), m.p. 146°-150° C.; NMR (d6 -DMSO); 1.25-1.35(m, 6H), 2.8(q, 2H), 3.35-3.45(m, 1H), 3.6(s, 2H), 5.4(s, 2H), 6.8-6.9(m, 6H), 7.05-7.15(m, 3H), 7.2-7.4(m, 10H), 7.45-7.6(m, 5H), 7.8(dd, 1H), 8.1(d, 1H).

Workup

  1. additionwere added
  2. stirringthe mixture was stirred for 30 minutes
  3. customThe insoluble solid was removed by filtration
  4. concentrationthe filtrate was concentrated by evaporation
  5. customThe residue was triturated with ether

Sources & evidence

ORD record
ord-a702a0267ff246fe8295aa8a5329a560
Source dataset
uspto-grants-1993_06
Patent number
US05219863

Reaction notes

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