Morpholine → HCID 23151000, compound

HRID 1984725Notes

Reaction equation

HRID 1984725 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]([C:14]2[C:15]([S:20][CH:21]([NH:28][C:29](=[O:32])[CH2:30]Cl)[C:22]3[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=3)=[N:16][CH:17]=[CH:18][CH:19]=2)=[O:13])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C(OCC)(=O)C.[NH:39]1[CH2:44][CH2:43][O:42][CH2:41][CH2:40]1>>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]([C:14]2[C:15]([S:20][CH:21]([NH:28][C:29](=[O:32])[CH2:30][N:39]3[CH2:44][CH2:43][O:42][CH2:41][CH2:40]3)[C:22]3[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=3)=[N:16][CH:17]=[CH:18][CH:19]=2)=[O:13])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 8083MorpholineHCID 8857Ethyl AcetateHCID 68844582HCID 68844582, compound

Product 1

HCID 23151000HCID 23151000, compoundYield 32%

Conditions

Temperature
80 °C

Procedure

N-(4-tert-Butylphenyl)-2-(2-chloroacetylaminopyridin-4-ylmethylthio)pyridine-3-carboxamide (Compound No. 16-1, 50 mg, 0.11 mmol) was suspended in morpholine (1.0 mL), and the mixture was stirred for 2 hours at 80° C. in the sealed tube. Ethyl acetate (50 mL) was added to the reaction mixture, the whole was washed with water (50 mL) and brine (50 mL), and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, the resulting solid was filtered off with diethyl ether and dried under reduced pressure to give 17 mg of the target compound as a pale yellow solid. (Yield 32%)

Workup

  1. washthe whole was washed with water (50 mL) and brine (50 mL)
  2. dry with materialdried over anhydrous sodium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. filtrationthe resulting solid was filtered off with diethyl ether
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-9720ca148f6f41b39caa6e8e9b42ef3f
Source dataset
uspto-grants-2009_06
Patent number
US07544703B2

Reaction notes

Loading…