1,4-Dioxane → HCID 178490066, compound

HRID 1349689Notes

Reaction equation

HRID 1349689 reaction equation
O1CCCCC1[N:7]1[C:15]2[C:10](=[CH:11][C:12]([C:16]3[N:20]=[CH:19][N:18](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[N:17]=3)=[CH:13][CH:14]=2)[C:9](/[CH:40]=[CH:41]/[C:42]2C=C[C:45](OC)=[CH:44][CH:43]=2)=[N:8]1.O1[CH2:55][CH2:54][O:53][CH2:52]C1>Cl>[NH:18]1[CH:19]=[N:20][C:16]([C:12]2[CH:11]=[C:10]3[C:15](=[CH:14][CH:13]=2)[NH:7][N:8]=[C:9]3/[CH:40]=[CH:41]/[C:42]2[CH:55]=[C:54]([O:53][CH3:52])[CH:45]=[CH:44][CH:43]=2)=[N:17]1

Participants

4

Reactant 2

HCID 312751,4-DioxaneHCID 86591921HCID 86591921, compound

Product 1

HCID 178490066HCID 178490066, compoundYield 17.4%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent2×

Procedure

Hydrolysis was performed by stirring 1-((1E)-2-{1-perhydro-2H-pyran-2-yl-5-[1-(triphenylmethyl)(1,2,4-triazol-3-yl)](1H-indazol-3-yl)}vinyl-4-methoxybenzene 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. A mixture of 2 isomers was isolated after purification by preparative HPLC (3% of the minor isomer) (0.014 g, 17.4% yield) 1H NMR (DMSO-d6) δ 8.8 (s, 1H), 8.55 (s, 1H), 8.15 (d, 1H), 7.7 (t, 3H), 7.5 (d, 2H), 7.0 (d, 2H), 3.8 (s, 3H); ES-MS (m/z) 318 [M+1]+.

Workup

  1. customHydrolysis
  2. additionA mixture of 2 isomers
  3. customwas isolated
  4. customafter purification by preparative HPLC (3% of the minor isomer) (0.014 g, 17.4% yield) 1H NMR (DMSO-d6) δ 8.8 (s, 1H), 8.55 (s, 1H), 8.15 (d, 1H), 7.7 (t, 3H), 7.5 (d, 2H), 7.0 (d, 2H), 3.8 (s, 3H)

Sources & evidence

ORD record
ord-ce3280f600dc4ecfb79bdbd9ff8c1aba
Source dataset
uspto-grants-2007_05
Patent number
US07211594B2

Reaction notes

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