Toluene → HCID 20789021, compound

HRID 2183363Notes

Reaction equation

HRID 2183363 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)-1-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-58742d488175494fb57792924bae4f9c
Source dataset
uspto-grants-2005_05
Patent number
US06897231B2

Reaction notes

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