Ethyl orthoformate → HCID 86727108, compound

HRID 2175923Notes

Reaction equation

HRID 2175923 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[CH2:10][CH2:9][CH:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:5]2=[N:6][CH:7]=1.[CH:16](OCC)(OCC)OCC.[N-:26]=[N+:27]=[N-:28].[Na+]>C(O)(=O)C>[N:1]1([C:2]2[CH:3]=[C:4]3[CH2:10][CH2:9][CH:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:5]3=[N:6][CH:7]=2)[CH:16]=[N:28][N:27]=[N:26]1

Participants

5

Reactant 3

HCID 31214Ethyl orthoformateHCID 33557Sodium AzideHCID 86727107HCID 86727107, compound

Product 1

HCID 86727108HCID 86727108, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of ethyl 3-amino-6,7-dihydro-5H-cyclopenta[b]pyridine-7-carboxylate (3.0 g, 14.6 mmol) and triethyl orthoformate (6.5 g, 43.6 mmol) in 50 mL of acetic acid was added sodium azide (1.0 g, 16.0 mmol). The mixture was heated to 100° C. for 3 hours. The reaction was complete by TLC. The reaction mixture was cooled to room temperature. The solvent was removed under vacuum. The residue was dissolved in EtOAc, washed with water, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by column chromatography to afford the title compound

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customThe solvent was removed under vacuum
  3. dissolutionThe residue was dissolved in EtOAc
  4. washwashed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-33f93ec77f3046c1aec8666af5855a13
Source dataset
uspto-grants-2015_06
Patent number
US09062070B2

Reaction notes

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