HCID 10780459, compound → HCID 21309707, compound

HRID 617353Notes

Reaction equation

HRID 617353 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([O:8][CH2:9][C@@H:10]2[CH2:13][CH2:12][N:11]2[C:14](OC(C)(C)C)=O)[CH:5]=[N:6][CH:7]=1>C=O.C(O)=O>[Cl:1][C:2]1[CH:3]=[C:4]([O:8][CH2:9][C@@H:10]2[CH2:13][CH2:12][N:11]2[CH3:14])[CH:5]=[N:6][CH:7]=1

Participants

4

Reactant 1

HCID 10780459HCID 10780459, compound

Product 1

HCID 21309707HCID 21309707, compound

Reagents, catalysts & solvents 2

HCID 284Formic AcidSolventHCID 712FormaldehydeSolvent

Procedure

A 500 mg sample of 5-chloro-3-(N-t-butoxycarbonyl-2-(S)-azetidinylmethoxy)pyridine, prepared as in Example 39a above, was dissolved in 3 mL of 37% HCHO and 1.5 mL of HCOOH, and the reaction mixture was stirred at 100° C. for 40 minutes. The reaction was quenched by addition of H2O. The mixture was adjusted to pH 7 with NaHCO3 and extracted with methylene chloride, the extract was dried over MgSO4, and the solvent was removed to give the title compound (181 mg). MS (DCI/NH3) m/e: 213/215 (M+H)+. 1H NMR (CDCl3, 300MHz) δ: 8.22 (d, J=2.5 Hz, 1H), 8.17 (d, J=1.9 Hz, 1H), 7.23 (dd, J=2.5, 1.9 Hz, 1H), 4.01 (d, J=5.1 Hz, 2H), 3.52-3.44 (m, 1H), 3.45-3.35 (m, 1H), 2.94-2.83 (m, 1H), 2.41 (s, 3H), 2.15-2.04 (m, 2H).

Workup

  1. customThe reaction was quenched by addition of H2O
  2. extractionextracted with methylene chloride
  3. dry with materialthe extract was dried over MgSO4
  4. customthe solvent was removed

Sources & evidence

ORD record
ord-5af3c87505c143f4a515a47d46cb162b
Source dataset
uspto-grants-1999_09
Patent number
US05948793

Reaction notes

Loading…