HCID 68752526, compound → HCID 178451787, compound

HRID 1851250Notes

Reaction equation

HRID 1851250 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14](=O)[NH:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]#[N:23])=[CH:18][C:17]=2[NH2:24])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CCO.[OH-].[Na+]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[NH:15][C:16]3[CH:21]=[CH:20][C:19]([C:22]#[N:23])=[CH:18][C:17]=3[N:24]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 68752526HCID 68752526, compound

Product 1

HCID 178451787HCID 178451787, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 4-(2-amino-4-cyano-phenylcarbamoyl)-piperidine-1-carboxylic acid tert-butyl ester (6 g) in EtOH (61 mL) and 2M aq. NaOH solution (61 mL) was heated at 75° C. (bath temperature) overnight. The heating was discontinued, the reaction was chilled (ice water bath) and quenched by pouring into saturated aq. citric acid solution (250 mL). The mixture was extracted with CH2Cl2 (5×) and the combined organic extract was dried (Na2SO4), filtered and concentrated in vacuo.

Workup

  1. customquenched
  2. additionby pouring into saturated aq. citric acid solution (250 mL)
  3. extractionThe mixture was extracted with CH2Cl2 (5×)
  4. extractionthe combined organic extract
  5. dry with materialwas dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a4154bec75784e3d97d0174b820a0e05
Source dataset
uspto-grants-2015_02
Patent number
US08957064B2

Reaction notes

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