Toluene → HCID 20789021, compound

HRID 1349865Notes

Reaction equation

HRID 1349865 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-a2bec3bcebd04c4ea1280a4976030552
Source dataset
uspto-grants-2007_05
Patent number
US07211594B2

Reaction notes

Loading…