HCID 88575710, compound → HCID 66692552, compound

HRID 713700Notes

Reaction equation

HRID 713700 reaction equation
[CH2:1]([O:8][C:9](/[N:11]=[C:12]1/[N:13](C(OCC2C=CC=CC=2)=O)[C:14]([CH2:18][C:19](N(OC)C)=[O:20])=[CH:15][CH:16]=[CH:17]/1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:35]([Mg]Br)=[CH2:36]>C1COCC1>[CH2:1]([O:8][C:9](=[O:10])[NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][C:19](=[O:20])[CH:35]=[CH2:36])[N:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 88575710HCID 88575710, compoundHCID 178418507HCID 178418507, compound

Product 1

HCID 66692552HCID 66692552, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of benzyl (2E)-2-([(benzyloxy)carbonyl]imino)-6-(2-[methoxy(methyl)amino]-2-oxoethyl)pyridine-1(2H)-carboxylate (150 mg, 0.33 mmol) in 4 ml anhydrous THF cooled to −40° C. via dry ice/acetone bath under nitrogen atmosphere was added via syringe 1.0M vinylmagnesium bromide (1.5 mL, 1.5 mmol) and the resulting solution stirred for 2 hours allowing to warm to room temperature. The reaction was quenched with water and extracted with ethyl acetate (3×10 mL). The organics were combined, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified via preparative TLC plate (1000 μM) eluting with 2.5% methanol in dichloromethane to afford the title compound (64 mg, 67%). LC-MS: C17H16N2O3 calculated 296.32 found m/z (ES) 297.3 (MH)+. 1HNMR (500 MHz, DMSO) δ: 10.12 (s, 1H) 8.05 (d, J=8.5 Hz, 1H), 7.99 (d, J=2.1, 1H), 7.62 (dd, J=2.2, 8.7 Hz, 1H), 7.60-7.34 (m, 5H), 6.40 (dd, J=10.3, 17.7 Hz, 1H), 6.26 (dd, J=10.3, 18.1 Hz, 1H), 5.94 (d, J=10.3 Hz, 1H), 5.22 (s, 2H), 3.60 (s, 2H).

Workup

  1. customThe reaction was quenched with water
  2. extractionextracted with ethyl acetate (3×10 mL)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified via preparative TLC plate (1000 μM)
  7. washeluting with 2.5% methanol in dichloromethane

Sources & evidence

ORD record
ord-ea3dc4c97f4f4074b74ceeca1824a93e
Source dataset
uspto-grants-2015_11
Patent number
US09186354B2

Reaction notes

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