HCID 10780459, compound → HCID 21309707, compound

HRID 1416641Notes

Reaction equation

HRID 1416641 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 The mixture
  2. extractionextracted with methylene chloride
  3. dry with materialthe extract was dried over MgSO4
  4. customthe solvent was removed

Sources & evidence

ORD record
ord-4670540fe0d54bd1bc8e21e7c83eee73
Source dataset
uspto-grants-1999_06
Patent number
US05914328

Reaction notes

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