Potassium Carbonate → HCID 178513431, compound

HRID 68767Notes

Reaction equation

HRID 68767 reaction equation
[C:1]([N:3]1[CH2:8][CH2:7][CH:6]([N:9]([CH:23]2[CH2:25][CH2:24]2)[C:10](=[O:22])[C:11]2[CH:16]=[CH:15][C:14]([C:17]3[O:21][CH:20]=[N:19][CH:18]=3)=[CH:13][CH:12]=2)[CH2:5][CH2:4]1)#[N:2].Cl.[NH2:27][OH:28].C(=O)([O-])[O-].[K+].[K+]>C(O)C.O>[CH:23]1([N:9]([CH:6]2[CH2:7][CH2:8][N:3]([C:1](=[NH:2])[NH:27][OH:28])[CH2:4][CH2:5]2)[C:10](=[O:22])[C:11]2[CH:12]=[CH:13][C:14]([C:17]3[O:21][CH:20]=[N:19][CH:18]=3)=[CH:15][CH:16]=2)[CH2:25][CH2:24]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 86678209N-(1-Cyano-piperidin-4-yl)-N-cyclopropyl-4-oxazol-5-yl-benzamide

Product 1

HCID 178513431HCID 178513431, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of N-(1-cyano-piperidin-4-yl)-N-cyclopropyl-4-oxazol-5-yl-benzamide (200 mg), hydroxylamine hydrochloride (70 mg), and potassium carbonate (82 mg) in ethanol (0.70 mL) and water (1.00 mL) is heated under reflux for 5 h. The reaction mixture is cooled to room temperature, stirred at this temperature for two days and concentrated in vacuo. The residue is mixed with water and ethyl acetate and the organic phase is separated, dried and concentrated in vacuo. The crude product is purified by HPLC (MeOH/H2O/TFA). LC (method 3): tR=1.35 min; Mass spectrum (ESI+): m/z=370 [M+H]+.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 5 h
  3. concentrationconcentrated in vacuo
  4. additionThe residue is mixed with water and ethyl acetate
  5. customthe organic phase is separated
  6. customdried
  7. concentrationconcentrated in vacuo
  8. customThe crude product is purified by HPLC (MeOH/H2O/TFA)

Sources & evidence

ORD record
ord-b4d154b874694d7bb70674d22f0a7ae6
Source dataset
uspto-grants-2014_09
Patent number
US08822471B2

Reaction notes

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