Sodium Bicarbonate → HCID 131721101, compound

HRID 361590Notes

Reaction equation

HRID 361590 reaction equation
[N:1]1([CH:6]([C:20]2[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=2)/[CH:7]=[CH:8]/[C:9]2[N:14]=[C:13](/[CH:15]=[CH:16]/[C:17]([OH:19])=[O:18])[CH:12]=[CH:11][CH:10]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:27](=O)([O-])O.[Na+]>CO>[CH3:27][O:18][C:17](=[O:19])/[CH:16]=[CH:15]/[C:13]1[CH:12]=[CH:11][CH:10]=[C:9](/[CH:8]=[CH:7]/[CH:6]([C:20]2[CH:21]=[CH:22][C:23]([CH3:26])=[CH:24][CH:25]=2)[N:1]2[CH2:2][CH2:3][CH2:4][CH2:5]2)[N:14]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 131721102HCID 131721102, compound

Product 1

HCID 131721101HCID 131721101, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of (E)-3-(6-[3-pyrrolidin-1-yl-{4-tolyl}-prop-1E-enyl]-pyridin-2-yl)-acrylic acid (2.04 g, 5.9 mmol) in methanol (50 ml) was treated with concentrated HCI (10 ml) and stirred at room temperature for 6 days. The reaction was neutralised with a saturated solution of sodium hydrogen carbonate and solvent removed under reduced pressure. DCM was added to the residue and inorganic solids removed by filtration. Concentration of the filtrate under reduced pressure yielded methyl-(E)-3-(6-[3-pyrrolidin-1-yl-{4-tolyl}-prop-1E-enyl]-pyridin-2-yl)-acrylate as a pink foam (1.98 g, 93%). 1H-NMR; δ (CDCl3), 7.70 (1H, d, J=15.7 Hz), 7.57 (1H, t, J=7.7 Hz), 7.30 (1H, t, J=7.6 Hz), 7.25 (2H, d, J=8.3 Hz), 7.17 (1H, d, J=7.2 Hz), 7.10 (2H, dt, J=8.2, 1.8 Hz), 6.96 (1H, d, J=15.6 Hz), 6.93 (1H, d, J=7.9 Hz), 3.83 (3H, s), 3.65 (2H, bs), 2.85 (4H, bm), 2.41 (3H, s) and 2.04 (4H, bm).

Workup

  1. customremoved under reduced pressure
  2. additionDCM was added to the residue and inorganic solids
  3. customremoved by filtration

Sources & evidence

ORD record
ord-1794edf81a7a4791a2fc742a8458a753
Source dataset
uspto-grants-1999_02
Patent number
US05866588

Reaction notes

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