Sodium Hydroxide → HCID 70800717, compound

HRID 2038798Notes

Reaction equation

HRID 2038798 reaction equation
[OH-].[Na+].[C:3]([O:7][C:8](=[O:17])[NH:9][C:10]1([C:14](=O)[CH3:15])[CH2:13][CH2:12][CH2:11]1)([CH3:6])([CH3:5])[CH3:4].[I:18][C:19]1[CH:20]=[C:21]([CH:26]=O)[C:22]([NH2:25])=[N:23][CH:24]=1>CCO>[C:3]([O:7][C:8](=[O:17])[NH:9][C:10]1([C:14]2[CH:15]=[CH:26][C:21]3[C:22](=[N:23][CH:24]=[C:19]([I:18])[CH:20]=3)[N:25]=2)[CH2:13][CH2:12][CH2:11]1)([CH3:6])([CH3:5])[CH3:4]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 177501772-Amino-5-iodopyridine-3-carbaldehydeHCID 675080291257639-06-7

Product 1

HCID 70800717HCID 70800717, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Freshly ground NaOH (0.32 g, 7.9 mmol) was dissolved in absolute EtOH (25 mL). To this solution was added (1-acetyl-cyclobutyl)-carbamic acid tert-butyl ester (0.84 g, 3.95 mmol) and 5-iodo-2-aminopyridine-3-carboxaldehyde (0.932 g, 3.76 mmol) simultaneously as a solution in EtOH (25 mL). The reaction was allowed to stir for 72 h and the volatiles were removed in vacuo. This crude residue was diluted with CH2Cl2, absorbed onto SiO2 by removal of solvent in vacuo and purified via SiO2 flash chromatography (20-75% EtOAc-hexane) to afford the title compound as a white solid (1.34 g, 84%), m/z=366.4.

Workup

  1. customthe volatiles were removed in vacuo
  2. additionThis crude residue was diluted with CH2Cl2
  3. customabsorbed onto SiO2 by removal of solvent in vacuo
  4. custompurified via SiO2 flash chromatography (20-75% EtOAc-hexane)

Sources & evidence

ORD record
ord-bde19b3b43b54898a1c8f7e9919e775c
Source dataset
uspto-grants-2013_11
Patent number
US08575360B2

Reaction notes

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