Methanol → HCID 178451665, compound

HRID 1851242Notes

Reaction equation

HRID 1851242 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([C:12]([NH:14][NH2:15])=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=1)#[N:17].C[O-].[Na+].CO>C(OCCO)C.C(O)(=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([C:12]2[N:17]=[C:16]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=3)[NH:15][N:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 887MethanolHCID 7522Pyridine-2-carbonitrileHCID 10942334Sodium MethoxideHCID 46835551tert-Butyl 3-(hydrazinecarbonyl)azetidine-1-carboxylate

Product 1

HCID 178451665HCID 178451665, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8076Glycol monoethyl etherSolvent

Conditions

Temperature
130 °C

Procedure

3-hydrazinocarbonyl-azetidine-1-carboxylic acid tert-butyl ester (2.74 g, 12.73 mmol) and 2-cyano-pyridine (1.45 g, 13.95 mmol) were dissolved in 2-ethoxyethanol (30 mL) and a 30 wt % solution of NaOMe in MeOH (1.19 mL, 6.38 mmol) was added. The resulting mixture was heated to 130° C. and stirred overnight. On cooling the mixture was neutralised by the addition of acetic acid and partitioned between EtOAc and saturated aqueous NaHCO3 solution. The organic phase was dried (Na2SO4) and concentrated in vacuo to give a yellow solid. Further purification was achieved by trituration with diethyl ether followed by recrystallisation from MeOH.

Workup

  1. temperatureOn cooling the mixture
  2. custompartitioned between EtOAc and saturated aqueous NaHCO3 solution
  3. dry with materialThe organic phase was dried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customto give a yellow solid
  6. customFurther purification
  7. customfollowed by recrystallisation from MeOH

Sources & evidence

ORD record
ord-bceec2103c2542d9ad4fd7437582aa9e
Source dataset
uspto-grants-2015_02
Patent number
US08957064B2

Reaction notes

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