Potassium Hydroxide → HCID 19771715, compound

HRID 1614590Notes

Reaction equation

HRID 1614590 reaction equation
[CH2:1]([C:3]1[CH:12]=[C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[C:27]3[N:28]=[N:29][N:30]([C:32]([C:45]4[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=4)([C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=4)[C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)[N:31]=3)=[CH:17][CH:16]=2)[C:10]2[N:9](C(=O)C(F)(F)F)[CH2:8][CH2:7][CH2:6][C:5]=2[N:4]=1)[CH3:2].[OH-].[K+]>CO>[CH2:1]([C:3]1[CH:12]=[C:11]([O:13][CH2:14][C:15]2[CH:16]=[CH:17][C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[C:27]3[N:28]=[N:29][N:30]([C:32]([C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)([C:39]4[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=4)[C:45]4[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=4)[N:31]=3)=[CH:19][CH:20]=2)[C:10]2[NH:9][CH2:8][CH2:7][CH2:6][C:5]=2[N:4]=1)[CH3:2]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 19771698HCID 19771698, compound

Product 1

HCID 19771715HCID 19771715, compoundYield 32.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of compound B5 (0.42 g) and potassium hydroxide (0.1 g) in methanol (5 ml) was left to stand for 1 hour. The solvent was removed by evaporation and the residue partitioned between ethyl acetate (20 ml) and water (20 ml). The organic phase was separated, washed with saturated sodium chloride solution (20 ml) and dried (MgSO4) The solvent was removed by evaporation and ether (10 ml) was added to the residue. Insoluble material was removed by filtration and the filtrate was evaporated to give 2-ethyl 5,6,7,8-tetrahydro-4-(2'-(2-triphenylmethyl-2H-tetrazol-5-yl)biphenyl)-4-yl)methoxy]-1,5-naphthyridine (A5) (0.12 g), as a foam; NMR (d6 -DMSO): 1.15(t,3H), 1.8-1.9(m,2H), 2.5(q,2H), 2.7(t,2H), 3.05-3.15(m,2H), 5.05(s,2H), 6.65(s,1H), 6.8-6.9(m,6H), 7.1(d,2H), 7.2-7.7(complex m,14H), 7.9(dd,1H).

Workup

  1. customThe solvent was removed by evaporation
  2. customthe residue partitioned between ethyl acetate (20 ml) and water (20 ml)
  3. customThe organic phase was separated
  4. washwashed with saturated sodium chloride solution (20 ml)
  5. dry with materialdried (MgSO4) The solvent
  6. customwas removed by evaporation and ether (10 ml)
  7. additionwas added to the residue
  8. customInsoluble material was removed by filtration
  9. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-188d63d0ecc54059bba29a7a35621b56
Source dataset
uspto-grants-1993_03
Patent number
US05198434

Reaction notes

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