Sodium Bicarbonate → HCID 68614940, compound

HRID 2189137Notes

Reaction equation

HRID 2189137 reaction equation
C([SiH2]O[C:7](C)(C)[C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][C:9]=1[C:15]1([OH:24])[CH2:20][CH2:19][CH2:18][N:17]2[CH:21]=[N:22][CH:23]=[C:16]12)(C)(C)C.C(=O)(O)[O-].[Na+]>Cl>[Cl:14][C:11]1[CH:12]=[CH:13][C:8]2[CH2:7][O:24][C:15]3([CH2:20][CH2:19][CH2:18][N:17]4[CH:21]=[N:22][CH:23]=[C:16]34)[C:9]=2[CH:10]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 131730083HCID 131730083, compound

Product 1

HCID 68614940HCID 68614940, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
95 °C

Procedure

A suspension of 2.672 mmol of 8-[2-(tert-butyl-dimethyl-silanyloxymethyl)-5-chloro-phenyl]-5,6,7,8-tetrahydro-imidazo[1,5-a]pyridin-8-ol in 40 ml of 1N aqueous HCl is stirred at 95° C. for 40 hours, then cooled to room temperature. The mixture is basified to pH 12 by dropwise addition of aqueous saturated sodium bicarbonate solution, and then extracted with dichloromethane (3×140 ml). The combined organic phases are dried over sodium sulfate, filtered and concentrated under reduced pressure. The resulting residue is purified by flash chromatography (SiO2 60 F) to afford the title compound as a beige solid. Rf=0.14 (EtOAc-methanol 10:1); Rt=3.04 (gradient I).

Workup

  1. temperaturecooled to room temperature
  2. extractionextracted with dichloromethane (3×140 ml)
  3. dry with materialThe combined organic phases are dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue is purified by flash chromatography (SiO2 60 F)

Sources & evidence

ORD record
ord-4537fe9794ab4d4f94f9f2d9f2d68ff9
Source dataset
uspto-grants-2012_12
Patent number
US08324235B2

Reaction notes

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