Hydrochloric Acid → HCID 59753744, compound

HRID 751730Notes

Reaction equation

HRID 751730 reaction equation
[C:1]1([CH2:7][C@H:8]([NH:20][C:21]([C:23]2[NH:32][C:26]3=[CH:27][N:28]=[C:29]([Cl:31])[CH:30]=[C:25]3[CH:24]=2)=[O:22])[C:9]2([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)OCC[O:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl>CC(C)=O>[CH2:7]([C@H:8]([NH:20][C:21]([C:23]1[NH:32][C:26]2=[CH:27][N:28]=[C:29]([Cl:31])[CH:30]=[C:25]2[CH:24]=1)=[O:22])[C:9](=[O:10])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 76852798HCID 76852798, compound

Product 1

HCID 59753744HCID 59753744, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 5-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid [2-phenyl-1-(S)-(2-phenyl-[1,3]dioxolan-2-yl)ethyl]amide (Preparation 96, 47 mg, 0.105 mmol) in acetone (20 mL) was added aqueous hydrochloric acid (1 mL, 1M). After stirring under reflux for 3 days the solvent was removed in vacuo. The residue was distributed between ethyl acetate (100 mL) and saturated sodium carbonate solution (50 mL). After separation the organic layer was washed with brine (50 ml), dried (MgSO4) and concentrated to a residue which was purified by flash chromatography on silica gel (eluent: hexane/ethyl acetate: 50/50) to give the title compound as colourless solid. m/z (ES+)=404.21 [M+H]+; RT=3.58 min.

Workup

  1. temperatureunder reflux for 3 days the solvent
  2. customwas removed in vacuo
  3. customAfter separation the organic layer
  4. washwas washed with brine (50 ml)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated to a residue which
  7. customwas purified by flash chromatography on silica gel (eluent: hexane/ethyl acetate: 50/50)

Sources & evidence

ORD record
ord-b7554c5a78c749b698bba09c43e72b2e
Source dataset
uspto-grants-2008_07
Patent number
US07405210B2

Reaction notes

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