Triethylamine → HCID 58530026, compound

HRID 451323Notes

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][C:41]([Br:44])=[CH:40][N: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][C:41]([Br:44])=[CH:40][N:39]=1)=[O:20])[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

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 (0.400 g, 1.448 mmol) in dry dichloromethane (17.66 mL) was added triethylamine (0.504 ml, 3.62 mmol), 2-chloro-1-methylpyridinium iodide (0.433 g, 1.694 mmol), and 2-amino-5-bromopyridine (0.311 g, 1.795 mmol) sequentially at room temperature under nitrogen. The reaction mixture was heated to 50° C. for 1 hour then purified on the mass directed HPLC (30×100 mm Waters Sunfire column; 5 micron; 50 ml/min; acetonitrile/water with 0.1% TFA over 15 min). Fractions containing the title compound were concentrated under vacuum then lyophilized overnight to afford the title compound as a yellow solid.

Workup

customthen purified on the mass
customHPLC (30×100 mm Waters Sunfire column; 5 micron; 50 ml/min; acetonitrile/water with 0.1% TFA over 15 min)
additionFractions containing the title compound
concentrationwere concentrated under vacuum

Sources & evidence

ORD record: ord-529de697dec94f8388c8638d43925fda
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08487093B2

Reaction notes

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