Hydrazine hydrate (1:1) → tert-Butyl 2-(4-(5-(4-chlorophenyl)-1H-pyrazol-3-yl)phenyl)morpholine-4-carboxylate

HRID 710238Notes

Reaction equation

HRID 710238 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH2:9][C:10]([C:12]2[CH:17]=[CH:16][C:15]([CH:18]3[O:23][CH2:22][CH2:21][N:20]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:19]3)=[CH:14][CH:13]=2)=O)=[CH:4][CH:3]=1.O.[NH2:33][NH2:34]>C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:34][N:33]=[C:10]([C:12]3[CH:17]=[CH:16][C:15]([CH:18]4[O:23][CH2:22][CH2:21][N:20]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:19]4)=[CH:14][CH:13]=3)[CH:9]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 89689396tert-Butyl 2-(4-(3-(4-chlorophenyl)-3-oxopropanoyl)phenyl)morpholine-4-carboxylate

Product 1

HCID 178452433tert-Butyl 2-(4-(5-(4-chlorophenyl)-1H-pyrazol-3-yl)phenyl)morpholine-4-carboxylateYield 100%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of tert-butyl 2-(4-(3-(4-chlorophenyl)-3-oxopropanoyl)phenyl)morpholine-4-carboxylate (210 mg, 0.473 mmol) and hydrazine hydrate (35.5 mg, 0.70 mmol) in ethanol (3.5 ml) was heated to reflux with stirring overnight. The clear yellow solution was evaporated under reduced pressure, water was added and ethyl acetate. The organic layer was separated, the aqueous layer was extracted again with ethyl acetate. The combined organic layers were dried over MgSO4 and evaporated. The crude material was purified by flash chromatography (10 g silica gel, 10 to 50% ethyl acetate in heptane) to yield a white solid (208 mg, 89%). MS (ISP neg): 438.3 ([{35Cl}M−H]+), 440.4 ([{37Cl}M−H]+).

Workup

  1. temperatureto reflux
  2. customThe clear yellow solution was evaporated under reduced pressure, water
  3. additionwas added
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was extracted again with ethyl acetate
  6. dry with materialThe combined organic layers were dried over MgSO4
  7. customevaporated
  8. customThe crude material was purified by flash chromatography (10 g silica gel, 10 to 50% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-53ebfc708966476589eb0a11e15c4f82
Source dataset
uspto-grants-2015_11
Patent number
US09181230B2

Reaction notes

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