Acetic Acid → HCID 67068467, compound

HRID 1171764Notes

Reaction equation

HRID 1171764 reaction equation
C(O)(=O)C.[CH2:5]([O:7][C:8]1[N:13]=[C:12]([CH:14]=O)[CH:11]=[CH:10][CH:9]=1)[CH3:6].[CH2:16]([O:18][C:19]([C:21]1[NH:22][CH:23]=[CH:24][C:25]=1[NH2:26])=[O:20])[CH3:17].[BH3-]C#N.[Na+]>C(O)C>[CH2:16]([O:18][C:19]([C:21]1[NH:22][CH:23]=[CH:24][C:25]=1[NH:26][CH2:14][C:12]1[CH:11]=[CH:10][CH:9]=[C:8]([O:7][CH2:5][CH3:6])[N:13]=1)=[O:20])[CH3:17]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 2773439Ethyl 3-amino-1H-pyrrole-2-carboxylateHCID 5003444Sodium cyanoborohydrideHCID 450837306-Ethoxypyridine-2-carbaldehyde

Product 1

HCID 67068467HCID 67068467, compoundYield 45.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Acetic acid (0.3 mL) was added to 6-ethoxy-pyridine-2-carbaldehyde (0.59 g, 3.9 mmol) and 3-amino-1H-pyrrole-2-carboxylic acid ethyl ester (0.30 g, 1.9 mmol) in ethanol (10 mL). After 1.5 h, NaCNBH3 (0.24 g, 3.9 mmol) was added, and the resulting mixture was stirred at ambient temperature for 19 h. The solvent was removed in vacuo, ethyl acetate was added to the residue, and insoluble material was removed by filtration. The filtrate was concentrated and the crude product was purified by flash column chromatography (heptane/ethyl acetate gradient; 0 to 35% ethyl acetate), obtaining 0.25 g (45%) of the title product as a solid.

Workup

  1. customThe solvent was removed in vacuo, ethyl acetate
  2. additionwas added to the residue, and insoluble material
  3. customwas removed by filtration
  4. concentrationThe filtrate was concentrated
  5. customthe crude product was purified by flash column chromatography (heptane/ethyl acetate gradient; 0 to 35% ethyl acetate)

Sources & evidence

ORD record
ord-c7e8d28c1fa545e5895c9b9bb003f50e
Source dataset
uspto-grants-2010_11
Patent number
US07829707B2

Reaction notes

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