Pyridine → HCID 69999528, compound

HRID 1634832Notes

Reaction equation

HRID 1634832 reaction equation
Cl[C:2](=[O:9])[CH2:3][CH2:4][C:5]([O:7][CH3:8])=[O:6].[CH3:10][O:11][CH:12]([O:32][CH3:33])[CH:13]1[CH2:18][CH2:17][N:16]([S:19]([C:22]2[CH:27]=[CH:26][C:25]([C:28](=[NH:31])[NH:29]O)=[CH:24][CH:23]=2)(=[O:21])=[O:20])[CH2:15][CH2:14]1.N1C=CC=CC=1>>[CH3:8][O:7][C:5](=[O:6])[CH2:4][CH2:3][C:2]1[O:9][N:31]=[C:28]([C:25]2[CH:26]=[CH:27][C:22]([S:19]([N:16]3[CH2:17][CH2:18][CH:13]([CH:12]([O:11][CH3:10])[O:32][CH3:33])[CH2:14][CH2:15]3)(=[O:21])=[O:20])=[CH:23][CH:24]=2)[N:29]=1

Participants

4

Reactant 3

HCID 1049PyridineHCID 73888Butanoic acid, 4-chloro-4-oxo-, methyl esterHCID 178499527HCID 178499527, compound

Product 1

HCID 69999528HCID 69999528, compound

Conditions

Temperature
85 °C

Procedure

Methyl 4-chloro-4-oxobutanoate (0.391 g, 2.6 mmol), 4-{[4-(dimethoxy-methyl)-1-piperidinyl]sulfonyl}-N-hydroxybenzenecarboximidamide (0.480 g, 1.3 mmol) was dissolved in 4 mL (49.5 mmol) of pyridine and stirred at 85° C. overnight. The solvent was evaporated with toluene, and the reaction mixture was partitioned between chloroform and water. The organic layer was washed with brine and dried with sodium sulfate. The final product was purified my flash chromatography (chloroform-methanol, 50:1) to give 0.130 g (0.22 mmol).

Workup

  1. customThe solvent was evaporated with toluene
  2. customthe reaction mixture was partitioned between chloroform and water
  3. washThe organic layer was washed with brine
  4. dry with materialdried with sodium sulfate
  5. customThe final product was purified my flash chromatography (chloroform-methanol, 50:1)
  6. customto give 0.130 g (0.22 mmol)

Sources & evidence

ORD record
ord-4b91ed3100f845a280df612e7e6c0476
Source dataset
uspto-grants-2003_01
Patent number
US06506901B2

Reaction notes

Loading…