Aminoacetaldehyde dimethyl acetal → HCID 178496002, compound

HRID 2046184Notes

Reaction equation

HRID 2046184 reaction equation
C[Al](C)C.[CH3:5][O:6][CH:7]([O:10][CH3:11])[CH2:8][NH2:9].C([O:14][C:15]([C:17]1[NH:18][N:19]=[C:20]([CH2:22][O:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:21]=1)=O)C>C1COCC1>[CH3:5][O:6][CH:7]([O:10][CH3:11])[CH2:8][NH:9][C:15]([C:17]1[NH:18][N:19]=[C:20]([CH2:22][O:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:21]=1)=[O:14]

Participants

5

Reactant 3

HCID 89728Aminoacetaldehyde dimethyl acetalHCID 16682925TrimethylaluminumHCID 178469067HCID 178469067, compound

Product 1

HCID 178496002HCID 178496002, compoundYield 144.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
130 °C

Procedure

Trimethylaluminum (1.7 mL, 3.4 mmol) was added to a stirred solution of aminoacetaldehyde dimethyl acetal (0.37 mL, 3.4 mmol) in THF (2 mL) at 0° C. under nitrogen atmosphere. To this solution 5-phenoxymethyl-2H-pyrazole-3-carboxylic acid ethyl ester (0.7 g, 2.84 mmol) in THF (5 mL) was added at 0° C. The reaction was heated at 130° C. for 2 minutes under microwave irradiation. Then mixture was quenched with a 2N solution of HCl (pH-3) and diluted with DCM. The organic layer was separated, dried (Na2SO4), filtered and the solvent evaporated in vacuo to yield 5-phenoxymethyl-2H-pyrazole-3-carboxylic acid (2,2-dimethoxy-ethyl)-amide (1.25 g, quantitative) as a brown oil that was used in the next step without further purification.

Workup

  1. customThen mixture was quenched with a 2N solution of HCl (pH-3)
  2. additiondiluted with DCM
  3. customThe organic layer was separated
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-f67879b6515841bca0823b5bbdf82066
Source dataset
uspto-grants-2013_11
Patent number
US08592422B2

Reaction notes

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