Sodium Hydroxide → HCID 178424071, compound

HRID 1272831Notes

Reaction equation

HRID 1272831 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2(C(C3CCCCO3)=O)[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:17]4[N:21]=[CH:20][N:19](C5C=CC(C)=C(C)C=5C)[N:18]=4)[CH:15]=3)[NH:10][NH:9]2)=[CH:4][CH:3]=1.[OH-].[Na+]>Cl.O1CCOCC1>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:17]4[N:21]=[CH:20][NH:19][N:18]=4)[CH:15]=3)[NH:10][N:9]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 69425736HCID 69425736, compound

Product 1

HCID 178424071HCID 178424071, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

2-{3-(4-Methylphenyl)-5-[1-(trimethylphenyl)(1,2,4-triazol-3-yl)]-1H-indazoyl}perhydro-2H-pyran (0.130 g, 0.216 mmol) was dissolved in 4 mL of 4.0 N HCl in dioxane and 2 mL of 6.0 N aqueous HCl were added. After 2 hours at room temperature, the reaction mixture was neutralized using aqueous sodium hydroxide (6.0 N) and the product was extracted with ethyl acetate. The extracts were dried under vacuum and dissolved in 5 mL of 6.0 N aqueous sodium hydroxide, side products extracted twice with diethyl ether. The aqueous phase was neutralized with 6.0 N HCl and the product was extracted with ethyl acetate. The crude was purified by preparative HPLC (15–80% acetonitrile in water) (0.024 g, 40% yield): 1H NMR (DMSO-d6) δ 13.4 (br s, 1H), 8.7 (s, 1H), 8.4 (br s, 1H), 8.1 (dd, 1H), 7.9 (d, 2H), 7.7 (d, 1H), 7.4 (d, 2H), 7.0 (d, 1H), 2.4 (s, 3H); ES-MS (m/z) 276 [M+1]+.

Workup

  1. extractionthe product was extracted with ethyl acetate
  2. customThe extracts were dried under vacuum
  3. dissolutiondissolved in 5 mL of 6.0 N aqueous sodium hydroxide
  4. extractionside products extracted twice with diethyl ether
  5. extractionthe product was extracted with ethyl acetate
  6. customThe crude was purified by preparative HPLC (15–80% acetonitrile in water) (0.024 g, 40% yield)

Sources & evidence

ORD record
ord-720d125a057d4cdfbbeaf33d20a2d331
Source dataset
uspto-grants-2007_04
Patent number
US07208513B2

Reaction notes

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