Toluene → HCID 20789021, compound

HRID 1273013Notes

Reaction equation

HRID 1273013 reaction equation
COC1C=CC(C2CCCOC2[N:15]2[C:23]3[C:18](=[CH:19][C:20]([C:24]4[N:28]=[C:27]([CH2:29][N:30]([CH3:32])[CH3:31])[NH:26][N:25]=4)=[CH:21][CH:22]=3)[CH:17]=[N:16]2)=CC=1.[C:33]1(C)[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.[O:40]1CCOC[CH2:41]1.Cl>>[CH3:41][O:40][C:33]1[CH:38]=[CH:37][C:36]([C:17]2[C:18]3[C:23](=[CH:22][CH:21]=[C:20]([C:24]4[N:28]=[C:27]([CH2:29][N:30]([CH3:31])[CH3:32])[NH:26][N:25]=4)[CH:19]=3)[NH:15][N:16]=2)=[CH:35][CH:34]=1

Participants

4

Reactant 3

HCID 1140TolueneHCID 204431481,4-Dioxane hydrochlorideHCID 69424032HCID 69424032, compound

Product 1

HCID 20789021HCID 20789021, compoundYield 20%

Procedure

({3-[3-(4-Methoxyphenyl)-perhydro-2H-pyran-2-yl(1H-indazol-5-yl)](1H-1,2,4-triazol-5-yl)}methyl)dimethylamine (0.57 g, 1.32 mmol) was suspended in 10 mL of 4 M in HCl dioxane solution. Toluene (10 mL) was added and the suspension was stirred at room temperature for 18 h. The reaction was quenched with saturated aqueous NaHCO3 solution and then concentrated under reduced pressure. The residue was taken up in DMSO and filtered. Purification by preparative HPLC (15–80% acetonitrile in water) furnished 92 mg (20% yield) of the title compound. 1H NMR (DMSOd6) δ 14.0 (s, 1H), 13.2 (s, 1H), 8.6 (s, 1H), 8.05 (dd, 1H), 7.95 (m, 2H), 7.65 (d, 1H), 7.14 (m, 2H), 3.8 (s, 3H), 3.6 (s, 2H), 2.2 (s, 6H); ES-MS (m/z) 349 [M+H]+.

Workup

  1. customThe reaction was quenched with saturated aqueous NaHCO3 solution
  2. concentrationconcentrated under reduced pressure
  3. filtrationfiltered
  4. customPurification by preparative HPLC (15–80% acetonitrile in water)

Sources & evidence

ORD record
ord-1c03270a772c41b4bee8428063d47485
Source dataset
uspto-grants-2007_04
Patent number
US07208513B2

Reaction notes

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