Water → HCID 21906225, compound

HRID 1882950Notes

Reaction equation

HRID 1882950 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH:14]=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:16][C:17]1[CH:32]=[CH:31][CH:30]=[CH:29][C:18]=1[C:19]([NH:21][C:22]1[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][N:23]=1)=[O:20].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.O>C1C=CC=CC=1>[Cl:28][C:25]1[CH:26]=[CH:27][C:22]([NH:21][C:19](=[O:20])[C:18]2[CH:29]=[CH:30][CH:31]=[CH:32][C:17]=2[N:16]=[CH:14][CH:11]2[CH2:10][CH2:9][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:13][CH2:12]2)=[N:23][CH:24]=1

Participants

6

Reactant 4

HCID 962WaterHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 1514430tert-Butyl 4-formylpiperidine-1-carboxylateHCID 219063812-amino-N-(5-chloropyridin-2-yl)benzamide

Product 1

HCID 21906225HCID 21906225, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution containing 1-tert-butoxycarbonyl-4-piperidinecarboxaldehyde (500 mg, 2.34 mmol), 2-amino-N-(5-chloropyridin-2-yl)benzamide (580 mg, 0.23 mmol), and pyridinium p-toluenesulfonate (58 mg, 0.23 mmol) in benzene (250 mL) was heated at reflux with azeotropic removal of water. After 16 h, the mixture was concentrated and the residue partitioned between EtOAc (300 mL) and water (150 mL). The organic phase was separated and washed again with water (150 mL), brine (150 mL); then dried with MgSO4, filtered and concentrated to afford, after purification by column chromatography (SiO2: 0 to 10% EtOAc:methylene chloride), 750 mg (72%) of the title compound.

Workup

  1. temperaturewas heated
  2. concentrationthe mixture was concentrated
  3. customthe residue partitioned between EtOAc (300 mL) and water (150 mL)
  4. customThe organic phase was separated
  5. washwashed again with water (150 mL), brine (150 mL)
  6. dry with materialthen dried with MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto afford
  10. customafter purification by column chromatography (SiO2: 0 to 10% EtOAc:methylene chloride), 750 mg (72%) of the title compound

Sources & evidence

ORD record
ord-60e888eb73254c81a215c9980e202aa1
Source dataset
uspto-grants-2004_07
Patent number
US06759414B2

Reaction notes

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