Acetic Acid → HCID 86725589, compound

HRID 514467Notes

Reaction equation

HRID 514467 reaction equation
[Si:1]([O:8][CH2:9][CH2:10]/[C:11](=[CH:16]\[N:17](C)C)/[C:12]([O:14][CH3:15])=[O:13])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[NH:20]([C:22]1[CH:27]=[C:26]([C:28]#[N:29])[CH:25]=[CH:24][N:23]=1)N.C(O)(=O)C.C([O-])(O)=O.[Na+]>C(O)C>[Si:1]([O:8][CH2:9][CH2:10]/[C:11](=[CH:16]\[NH:17][NH:20][C:22]1[CH:27]=[C:26]([C:28]#[N:29])[CH:25]=[CH:24][N:23]=1)/[C:12]([O:14][CH3:15])=[O:13])([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 201187142-Hydrazinylpyridine-4-carbonitrileHCID 86725587HCID 86725587, compound

Product 1

HCID 86725589HCID 86725589, compoundYield 68.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

Charged methyl (2E)-4-[tert-butyl(dimethyl)silyl]oxy-2-(dimethylaminomethylidene)butanoate (7.33 g, 50%, 12.72 mmol), 2-hydrazinopyridine-4-carbonitrile (1.70 g, 12.72 mmol), acetic acid (10 mL) and ethanol (50 mL) to a flask, the mixture was heated to 90° C. for 30 min, cooled to r.t. and basified with NaHCO3 at 0° C. to pH=8. It was then extracted with ethyl acetate twice, concentrated and purified by silica gel chromatograph (PE/EA=10/1) to give the title compound (3.3 g, 34%). 1H NMR (400 MHz, CDCl3): δ 0.04 (6H, d, J=1.6 Hz), 0.89 (9H, s), 1.96-2.17 (2H, m), 3.59 (1H, q, J=6.4 Hz), 3.69 (2H, d, J=6.0 Hz), 3.74 (3H, s), 6.91-6.92 (1H, m), 7.19 (1H, d, J=6.0 Hz), 7.38 (1H, s), 8.22 (1H, d, J=5.2 Hz), 8.33 (1H, s). [M+H] Calc'd for C18H28N4O3Si, 377. Found, 377.

Workup

  1. temperaturecooled to r.t.
  2. extractionIt was then extracted with ethyl acetate twice
  3. concentrationconcentrated
  4. custompurified by silica gel chromatograph (PE/EA=10/1)

Sources & evidence

ORD record
ord-f5ada3df00fc45b39e072fb4e3e591ff
Source dataset
uspto-grants-2015_08
Patent number
US09107916B2

Reaction notes

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