Triethylamine → HCID 21913341, compound

HRID 1352536Notes

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

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 2 hours, 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

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

Sources & evidence

ORD record: ord-73d4c84250794587966c8c62a96ce695
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07220758B2

Reaction notes

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