HCID 86585600, compound → HCID 178478076, compound

HRID 1349690Notes

Reaction equation

HRID 1349690 reaction equation
[Cl: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>[Cl:1][C:2]1[CH:7]=[CH:6][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:4][CH:3]=1

Participants

4

Reactant 1

HCID 86585600HCID 86585600, compound

Product 1

HCID 178478076HCID 178478076, compoundYield 56.6%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

Hydrolysis was performed by stirring 2-{3-[(1E)-2-(4-chlorophenyl)vinyl]-5-[1-(triphenylmethyl)(1,2,4-triazol-3-yl)]-1H-indazoyl}perhydro-2H-pyran 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 was isolated as a 98:2 mixture of isomers (0.040 g, 56.6% yield): 1H NMR (DMSO-d6) δ 14.4, 14.0 (2s, 1H), 13.4, 13.3 (2s, 1H), 8.7 (m, 1H), 8.1 (m, 2H), 7.8–7.4 (m, 7H); ES-MS (m/z) 322 [M+1]+.

Workup

  1. customHydrolysis
  2. customThe title compound was purified by column chromatography (5% MeOH in dichloromethane)
  3. customwas isolated as a 98:2 mixture of isomers (0.040 g, 56.6% yield)

Sources & evidence

ORD record
ord-49e5fc0442c448f99b528005dad26e7d
Source dataset
uspto-grants-2007_05
Patent number
US07211594B2

Reaction notes

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