4-Aminopyridine → HCID 58530129, compound

HRID 451306Notes

Reaction equation

HRID 451306 reaction equation
[C:1]1([CH2:7][O:8][N:9]2[C:15](=[O:16])[N:14]3[CH2:17][C@H:10]2[CH2:11][CH2:12][C@H:13]3[C:18]([OH:20])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[I-].ClC1C=CC=C[N+]=1C.[NH2:37][C:38]1[CH:43]=[CH:42][N:41]=[CH:40][CH:39]=1>ClCCl>[CH2:7]([O:8][N:9]1[C:15](=[O:16])[N:14]2[CH2:17][C@H:10]1[CH2:11][CH2:12][C@H:13]2[C:18]([NH:37][C:38]1[CH:43]=[CH:42][N:41]=[CH:40][CH:39]=1)=[O:20])[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 17274-AminopyridineHCID 8471TriethylamineHCID 1670692-Chloro-1-methylpyridinium iodideHCID 57389355(2S,5R)-6-(Benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxylic acid

Product 1

HCID 58530129HCID 58530129, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of (2S,5R)-6-(phenylmethoxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxylic acid (51.5 mg, 0.186 mmol) in dry dichloromethane (5 mL) was added triethylamine (0.065 mL, 0.466 mmol), 2-chloro-1-methylpyridinium iodide (63.4 mg, 0.248 mmol), and 4-aminopyridine (19.2 mg, 0.204 mmol) sequentially at room temperature under nitrogen. The reaction was then heated to 50° C. for 1.5 hours. LC/MS showed reaction complete. The reaction mixture was concentrated and purified by HPLC on a 30×100 mm Waters Sunfire column to afford the title compound as an orange solid after lyophilization.

Workup

  1. customreaction complete
  2. concentrationThe reaction mixture was concentrated
  3. custompurified by HPLC on a 30×100 mm Waters Sunfire column

Sources & evidence

ORD record
ord-c75565bf08f546d9af7e400d49b6e10a
Source dataset
uspto-grants-2013_07
Patent number
US08487093B2

Reaction notes

Loading…