Hydrazine hydrate (1:1) → HCID 89907187, compound

HRID 1506856Notes

Reaction equation

HRID 1506856 reaction equation
CO[C:3]([CH:5]1[O:10][C:9]([CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)([CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)[C:8]2[CH:23]=[C:24]([Cl:27])[CH:25]=[CH:26][C:7]=2[O:6]1)=[O:4].O.[NH2:29][NH2:30]>C(O)C>[Cl:27][C:24]1[CH:25]=[CH:26][C:7]2[O:6][CH:5]([C:3]([NH:29][NH2:30])=[O:4])[O:10][C:9]([CH:11]3[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]3)([CH:17]3[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]3)[C:8]=2[CH:23]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 72547172HCID 72547172, compound

Product 1

HCID 89907187HCID 89907187, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of 2.47 g 6-chloro-4,4-dicyclohexyl-4H-benzo[1,3]dioxine-2-carboxylic acid methyl ester in 9 ml ethanol was added to a solution of 0.61 ml hydrazine monohydrate in 9 ml ethanol. The reaction mixture was refluxed for 1 h. After cooling to room temperature, the solvent was removed in vacuo. The crude product was purified by preparative HPLC (C18 reverse phase column, elution with water/TFA gradient with 0.1% TFA). The fractions containing the product were evaporated and lyophilized to yield a solid. Yield: 1.1 g.

Workup

  1. temperatureThe reaction mixture was refluxed for 1 h
  2. customthe solvent was removed in vacuo
  3. customThe crude product was purified by preparative HPLC (
  4. washC18 reverse phase column, elution with water/TFA gradient with 0.1% TFA)
  5. additionThe fractions containing the product
  6. customwere evaporated
  7. customto yield a solid

Sources & evidence

ORD record
ord-3f4834f81c6a4a06bd67048ab6c2cbdd
Source dataset
uspto-grants-2015_12
Patent number
US09221784B2

Reaction notes

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