Sodium cyanoborohydride → HCID 58882957, compound

HRID 2364144Notes

Reaction equation

HRID 2364144 reaction equation
[NH2:1][C:2]1[C:3]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[N:4][CH:5]=[C:6]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:7]=1.O.[C:21]([OH:25])(=[O:24])[CH:22]=O.[BH3-]C#N.[Na+]>CCO>[CH2:8]([C:6]1[CH:7]=[C:2]([NH:1][CH2:22][C:21]([OH:25])=[O:24])[C:3]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[N:4][CH:5]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 5003444Sodium cyanoborohydrideHCID 15620607Glyoxylic acid, monohydrateHCID 42637771HCID 42637771, compound

Product 1

HCID 58882957HCID 58882957, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of ethyl 3-amino-5-benzylpyridine-2-carboxylate (0.543 g, 2.12 mmol) and glyoxylic acid monohydrate (0.254 g, 2.76 mmol) in EtOH (6 mL) was heated at reflux for 1 h. The mixture was allowed to cool to rt and NaCNBH3 (266 mg, 4.23 mmol) was added. After stirring 2 h at rt, the reaction was quenched with water and the EtOH was removed at reduced pressure. The aqueous mixture was extracted with CH2Cl2 and the organic layers were dried and concentrated. Trituration of the remaining material with EtOAc/hexanes and filtration afforded the product as a beige solid: 1H NMR (d6-DMSO) δ 13.2 (1H, br), 7.92 (1H, br t, J=4.8 Hz), 7.76 (1H, s), 7.26 (4H, m), 7.17 (1H, t, J=7 Hz), 7.00 (1H, s), 4.24 (2H, q, J=7 Hz), 3.90 (2H, s), 3.86 (2H, br), 1.27 (3H, t, J=7 Hz).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1 h
  3. customthe reaction was quenched with water
  4. customthe EtOH was removed at reduced pressure
  5. extractionThe aqueous mixture was extracted with CH2Cl2
  6. customthe organic layers were dried
  7. concentrationconcentrated
  8. filtrationTrituration of the remaining material with EtOAc/hexanes and filtration

Sources & evidence

ORD record
ord-f5a65ebe00e04219992726702eeddfb3
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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