Acetic Acid → HCID 67068502, compound

HRID 1171780Notes

Reaction equation

HRID 1171780 reaction equation
[O:1]=[C:2]1[NH:7][C:6]([CH:8]=O)=[CH:5][CH:4]=[CH:3]1.[CH2:10]([O:12][C:13]([C:15]1[NH:16][CH:17]=[CH:18][C:19]=1[NH2:20])=[O:14])[CH3:11].CC(O)=O.[BH3-]C#N.[Na+]>CCO>[CH2:10]([O:12][C:13]([C:15]1[NH:16][CH:17]=[CH:18][C:19]=1[NH:20][CH2:8][C:6]1[NH:7][C:2](=[O:1])[CH:3]=[CH:4][CH:5]=1)=[O:14])[CH3:11]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 2773439Ethyl 3-amino-1H-pyrrole-2-carboxylateHCID 5003444Sodium cyanoborohydrideHCID 220188131,6-Dihydro-6-oxopyridine-2-carboxaldehyde

Product 1

HCID 67068502HCID 67068502, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

6-Oxo-1,6-dihydropyridine-2-carbaldehyde (WO 2002/006272) (0.31 g, 2.5 mmol) was dissolved in EtOH (10 mL). 3-Amino-1H-pyrrole-2-carboxylic acid ethyl ester (0.19 g, 1.3 mmol) was added, followed by HOAc (0.14 mL, 2.5 mmol). The mixture was stirred for 75 minutes at r.t. and then NaCNBH3 (0.16 g, 2.5 mmol) was added. The reaction mixture was stirred at r.t. overnight. The solvent was evaporated in vacuo and the crude product was purified by flash column chromatography (CH2Cl2/methanol gradient; 0 to 10% methanol), obtaining 0.288 g (85%) of the title product as an oil that crystallized upon standing.

Workup

  1. stirringThe reaction mixture was stirred at r.t. overnight
  2. customThe solvent was evaporated in vacuo
  3. customthe crude product was purified by flash column chromatography (CH2Cl2/methanol gradient; 0 to 10% methanol)

Sources & evidence

ORD record
ord-c3f74a2618ea43eb931fa55cfb18c831
Source dataset
uspto-grants-2010_11
Patent number
US07829707B2

Reaction notes

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