3-Methoxypropanehydrazide → HCID 178494843, compound

HRID 541319Notes

Reaction equation

HRID 541319 reaction equation
C(S[N:4]=[CH:5][C:6]1[C:7]([CH:17]([CH3:19])[CH3:18])=[CH:8][C:9]([CH3:16])=[C:10]([CH:15]=1)[C:11]([O:13][CH3:14])=[O:12])C.[CH3:20][O:21][CH2:22][CH2:23][C:24]([NH:26][NH2:27])=O>C(O)(=O)C>[CH:17]([C:7]1[C:6]([C:5]2[NH:4][C:24]([CH2:23][CH2:22][O:21][CH3:20])=[N:26][N:27]=2)=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[C:9]([CH3:16])[CH:8]=1)([CH3:18])[CH3:19]

Participants

4

Reactant 2

HCID 27597273-Methoxypropanehydrazide2×HCID 86672536Methyl 5-((ethylthio)(imino)methyl)-4-isopropyl-2-methylbenzoate2×

Product 1

HCID 178494843HCID 178494843, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

Methyl 5-((ethylthio)(imino)methyl)-4-isopropyl-2-methylbenzoate (compound 198.4, 33 mg, 0.12 mmol, 1.0 equiv), 3-methoxypropanehydrazide (compound 143.1, 21 mg, 0.18 mmol, 1.5 equiv) and acetic acid (1.2 mL) were added to a 4-mL vial and heated at 80° C. with a loose cap for 4 hours. The solvent was removed in vacuo and the residue was dissolved in DCM (10 mL) and washed with saturated NaHCO3 (5 mL) then brine (5 mL), dried (Na2SO4), filtered and evaporated to a colorless oil (theoretical yield). m/z (ES+) 318 (M+H)+.

Workup

  1. customa loose cap for 4 hours
  2. customThe solvent was removed in vacuo
  3. dissolutionthe residue was dissolved in DCM (10 mL)
  4. washwashed with saturated NaHCO3 (5 mL)
  5. dry with materialbrine (5 mL), dried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated to a colorless oil (theoretical yield)

Sources & evidence

ORD record
ord-646c84b34c3042069b81d5fe9249e604
Source dataset
uspto-grants-2014_10
Patent number
US08871790B2

Reaction notes

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