Triethylamine → HCID 21913341, compound

HRID 1007995Notes

Reaction equation

HRID 1007995 reaction equation
C(N(CC)CC)C.[Cl:8][C:9]1[C:14]([NH2:15])=[C:13]([NH:16][CH2:17][CH2:18][O:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:12]([CH3:26])=[C:11]([CH3:27])[N:10]=1.[C:28](Cl)(=[O:33])[CH2:29][CH2:30][CH2:31][CH3:32]>C(#N)C>[Cl:8][C:9]1[C:14]([NH:15][C:28](=[O:33])[CH2:29][CH2:30][CH2:31][CH3:32])=[C:13]([NH:16][CH2:17][CH2:18][O:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:12]([CH3:26])=[C:11]([CH3:27])[N:10]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 61186Valeryl chlorideHCID 85898826HCID 85898826, compound

Product 1

HCID 21913341HCID 21913341, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

Triethylamine (1.39 ml), anhydrous acetonitrile (100 ml), and 2-chloro-5,6-dimethyl-N4-(2-phenoxyethyl)pyridine-3,4-diamine (2.92 g) from Part A of Example 2 were combined and cooled to 0° C. in an ice bath. Valeryl chloride (0.59 ml) was slowly added to the reaction mixture. After 2hours, the reaction mixture was heated to 55° C. for 24 hours, at which point HPLC analysis indicated the reaction was complete. The reaction mixture was cooled and the solvent was removed under reduced pressure. The resulting oil was dissolved in dichloromethane and washed with water. The organic layer was dried with magnesium sulfate and the solvent was removed under reduced pressure. The product was then passed through a silica gel column using 50/50 ethyl acetate/hexane as the eluant. The resulting light brown solid was used in the next step.

Workup

  1. temperaturethe reaction mixture was heated to 55° C. for 24 hours, at which point HPLC analysis
  2. temperatureThe reaction mixture was cooled
  3. customthe solvent was removed under reduced pressure
  4. dissolutionThe resulting oil was dissolved in dichloromethane
  5. washwashed with water
  6. dry with materialThe organic layer was dried with magnesium sulfate
  7. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-1d2f575928ef4c3cb22dcbcbbb8b2181
Source dataset
uspto-grants-2004_09
Patent number
US06797718B2

Reaction notes

Loading…