Hydrochloric Acid → HCID 91619103, compound

HRID 1502144Notes

Reaction equation

HRID 1502144 reaction equation
[C:1]([O:5][C:6](=[O:28])[CH2:7][C:8]1[CH:13]=[CH:12][N:11]=[C:10]([N:14]=C(C2C=CC=CC=2)C2C=CC=CC=2)[CH:9]=1)([CH3:4])([CH3:3])[CH3:2].Cl>C1COCC1.O>[NH2:14][C:10]1[CH:9]=[C:8]([CH2:7][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:28])[CH:13]=[CH:12][N:11]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 131734295HCID 131734295, compound

Product 1

HCID 91619103HCID 91619103, compound

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

tert-butyl{2-[(diphenylmethylidene)amino]-pyridin-4-yl}acetate (35 mg, 0.94 mmol) was dissolved in 1:1 mixture of THF/water (5 mL) and treated with 500 μL of a 1N aqueous hydrochloric acid solution. The reaction was allowed to stir at ambient temperature for 30 minutes and then concentrated in vacuo. The crude residue was dissolved in DCM and washed with a saturated aqueous sodium bicarbonate solution. The organic layers were dried over sodium sulfate, filtered and concentrated to afford crude title compound which was used without further purification: LC-MS: (M+H)+209.

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe crude residue was dissolved in DCM
  3. washwashed with a saturated aqueous sodium bicarbonate solution
  4. dry with materialThe organic layers were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-597632e3e078466c8a9b8cff2b76f918
Source dataset
uspto-grants-2015_12
Patent number
US09206199B2

Reaction notes

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