Hydrochloric Acid → HCID 178508479, compound

HRID 449061Notes

Reaction equation

HRID 449061 reaction equation
[NH2:1][C:2]1[C:3]2[N:4]([C:8]([C@H:24]3[CH2:27][C@H:26]([CH2:28][O:29]S(C4C=CC(C)=CC=4)(=O)=O)[CH2:25]3)=[N:9][C:10]=2[C:11]2[CH:16]=[CH:15][C:14]([O:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:13][CH:12]=2)[CH:5]=[CH:6][N:7]=1.[OH-].[K+].O.Cl>O1CCOCC1>[NH2:1][C:2]1[C:3]2[N:4]([C:8]([C@H:24]3[CH2:25][C@H:26]([CH2:28][OH:29])[CH2:27]3)=[N:9][C:10]=2[C:11]2[CH:12]=[CH:13][C:14]([O:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:15][CH:16]=2)[CH:5]=[CH:6][N:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14797Potassium HydroxideHCID 178427763HCID 178427763, compound

Product 1

HCID 178508479HCID 178508479, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of trans-toluene-4-sulfonic acid 3-[8-amino-1-(4-phenoxy-phenyl)-imidazo[1,5-a]pyrazin-3-yl]-cyclobutylmethyl ester (10.0 mg, 0.0185 mmol), potassium hydroxide (10.4 mg, 0.185 mmol), H2O (1 mL) and 1,4-dioxane (1 mL) was heated to 60° C. overnight. The mixture was titrated to pH 2 with 2M HCl. The dioxane was removed in vacuo. DCM was added to extract the product. The organics were combined, dried (Na2SO4) and removed under reduced pressure to give a residue which was then purified by flash chromatography (5% MeOH in DCM). MS (ES+): m/z 386.94 (100) [MH+]. HPLC: tR=2.23 min (polar—5 min).

Workup

  1. customThe dioxane was removed in vacuo
  2. additionDCM was added
  3. extractionto extract the product
  4. dry with materialdried (Na2SO4)
  5. customremoved under reduced pressure
  6. customto give a residue which
  7. customwas then purified by flash chromatography (5% MeOH in DCM)
  8. customHPLC: tR=2.23 min (polar—5 min)

Sources & evidence

ORD record
ord-afb96958321745718eda338dbdb48cab
Source dataset
uspto-grants-2013_07
Patent number
US08481733B2

Reaction notes

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