tert-Butanol → HCID 19367140, compound

HRID 1416300Notes

Reaction equation

HRID 1416300 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([CH2:11][N:12]3[CH2:17][CH2:16][N:15]([C:18]4[CH:25]=[CH:24][C:21]([C:22]#[N:23])=[CH:20][C:19]=4[F:26])[CH2:14][CH2:13]3)[N:10]=2)[CH:7]=1.[OH-].[Na+].C([OH:33])(C)(C)C>OO.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([CH2:11][N:12]3[CH2:17][CH2:16][N:15]([C:18]4[CH:25]=[CH:24][C:21]([C:22]([NH2:23])=[O:33])=[CH:20][C:19]=4[F:26])[CH2:14][CH2:13]3)[N:10]=2)[CH:7]=1

Participants

6

Reactant 3

HCID 6386tert-ButanolHCID 14798Sodium HydroxideHCID 19367096HCID 19367096, compound

Product 1

HCID 19367140HCID 19367140, compound

Reagents, catalysts & solvents 2

HCID 784Hydrogen PeroxideCatalystHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 4-[4-[(6-chloroimidazo[1,2-a]pyridin-2-yl)methyl]-1-piperazinyl]-3-fluorobenzonitrile (Example 38; 0.298 g), pulverized NaOH (0.159 g), tert-butanol (3 mL), and 5 drops of 30% hydrogen peroxide in water is heated at 90° C. for 5.5 h. The mixture is then concentrated under reduced pressure and the resulting solids are slurried in water, collected by filtration, and washed and dried under reduced pressure. The solids are then crystallized from dichloromethane/methanol to give 0.180 g of material, which is chromatographed on silica gel using methanol/dichloromethane (4/96). After combining and concentrating the appropriate fractions, the residue is crystallized from ethyl acetate/dichloromethane/methanol to give 0.084 g of the title compound; mp 253-255° C.; MS m/z 387, 389; IR (mineral oil) 1435, 1620, 1678, 1225, 1505 cm-1 ; 1H NMR (CDCl3 +CD3OD) δ2.77, 3.38, 3.80, 6.94, 7.19, 7.53, 7.62, 8.23.

Workup

  1. concentrationThe mixture is then concentrated under reduced pressure
  2. filtrationcollected by filtration
  3. washwashed
  4. customdried under reduced pressure
  5. customThe solids are then crystallized from dichloromethane/methanol

Sources & evidence

ORD record
ord-0a2c17244c6a47fca2b8d6ed628bfd61
Source dataset
uspto-grants-1999_06
Patent number
US05912246

Reaction notes

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