Ethyl orthoformate → HCID 67517614, compound

HRID 2173379Notes

Reaction equation

HRID 2173379 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]2[CH:8]([C:11]([O:13][CH3:14])=[O:12])[CH2:9][CH2:10][C:4]=2[CH:3]=1.[CH:15](OCC)(OCC)OCC.[N-:25]=[N+:26]=[N-:27].[Na+]>C(O)(=O)C.O.C(OCC)(=O)C>[N:1]1([C:2]2[N:7]=[CH:6][C:5]3[CH:8]([C:11]([O:13][CH3:14])=[O:12])[CH2:9][CH2:10][C:4]=3[CH:3]=2)[CH:15]=[N:27][N:26]=[N:25]1

Participants

7

Reactant 3

HCID 31214Ethyl orthoformateHCID 33557Sodium AzideHCID 67516395HCID 67516395, compound

Product 1

HCID 67517614HCID 67517614, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of methyl 3-amino-6,7-dihydro-5H-cyclopenta[c]pyridine-7-carboxylate (365 mg, 1.90 mmol), triethyl orthoformate (451 mg, 3.04 mmol), and sodium azide (185 mg, 2.85 mmol) in acetic acid (8 mL) was maintained in an oil bath heated at 80° C. for 3 h. After cooling to room temperature, the mixture was diluted with water and ethyl acetate and the layers separated. The aqueous was extracted with ethyl acetate (2×) and the combined organic layers were washed with brine, dried (Na2SO4), filtered and concentrated. Purification of the resulting residue (8−>80% EtOAc/hexanes eluent) provided methyl 3-(1H-tetrazol-1-yl)-6,7-dihydro-5H-cyclopenta[c]pyridine-7-carboxylate. 1H NMR (500 MHz, CDCl3), δ 9.54 (s, 1H), 8.55 (s, 1H), 8.00 (s, 1H), 4.22 (m, 1H), 3.82 (s, 3H), 3.30-3.06 (m, 2H), 2.66-2.49 (m, 2H); LC/MS (M+1)+=193.0;

Workup

  1. temperaturewas maintained in an oil bath
  2. temperatureAfter cooling to room temperature
  3. customthe layers separated
  4. extractionThe aqueous was extracted with ethyl acetate (2×)
  5. washthe combined organic layers were washed with brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customPurification of the resulting residue (8−>80% EtOAc/hexanes eluent)

Sources & evidence

ORD record
ord-17408c5fae4c4bbb9636d5cc7d6eaf97
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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