HCID 86591922, compound → HCID 178424875, compound

HRID 1353756Notes

Reaction equation

HRID 1353756 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]2(C(C3CCCCO3)=O)[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([C:19]4[N:23]=[CH:22][N:21](C(C5C=CC=CC=5)(C5C=CC=CC=5)C5C=CC=CC=5)[N:20]=4)[CH:17]=3)[NH:12][NH:11]2)=[CH:4][CH:3]=1>O1CCOCC1.Cl>[CH3:1][C:2]1[CH:3]=[CH:4][C:5](/[CH:8]=[CH:9]/[C:10]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([C:19]4[N:23]=[CH:22][NH:21][N:20]=4)[CH:17]=3)[NH:12][N:11]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 86591922HCID 86591922, compound

Product 1

HCID 178424875HCID 178424875, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

Hydrolysis was performed by stirring 2-{3-[(1E)-2-(4-methylphenyl)vinyl]-5-[1-(triphenylmethyl)(1,2,4-triazol-3-yl)]-1H-indazoyl}perhydro-2H-pyran (0.269 g, 0.42 mmol) in 4 mL of 4.0 N commercial solution of HCl in dioxane and 2 mL of 6.0 N aqueous HCl, at room temperature for 6.5 hours. The title compound was purified by column chromatography (5% MeOH in dichloromethane) and isolated as a 97:3 ratio of 2 isomers (0.103 g, 81% yield): 1H NMR (DMSO-d6) δ 8.8 (s, 1H), 8.6 (br s, 1H), 8.1 (d, 1H), 7.6 (m, 3H), 7.5 (d, 2H), 7.0 (d, 2H), 2.34 (s, 3H); ES-MS (m/z) 302 [M+1]+.

Workup

  1. customHydrolysis
  2. customThe title compound was purified by column chromatography (5% MeOH in dichloromethane)
  3. customisolated as a 97:3 ratio of 2 isomers (0.103 g, 81% yield)

Sources & evidence

ORD record
ord-e85db9324ad349da89235e0a41d535e6
Source dataset
uspto-grants-2007_05
Patent number
US07220771B2

Reaction notes

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