Triethylamine → HCID 22715001, compound

HRID 352013Notes

Reaction equation

[Cl:1][C:2]1[C:7]([NH2:8])=[C:6]([NH:9][CH2:10][CH:11]([CH3:13])[CH3:12])[CH:5]=[C:4]([CH3:14])[N:3]=1.C(N(CC)CC)C.[CH2:22]([O:24][CH2:25][C:26](Cl)=[O:27])[CH3:23]>ClCCl>[Cl:1][C:2]1[C:7]([NH:8][C:26](=[O:27])[CH2:25][O:24][CH2:22][CH3:23])=[C:6]([NH:9][CH2:10][CH:11]([CH3:12])[CH3:13])[CH:5]=[C:4]([CH3:14])[N:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Anhydrous dichloromethane (750 ml) and 2-chloro-N4-(2-methylpropyl)-6-methylpyridin-3,4-diamine (18.84 g) were combined and cooled to 0° C. Triethylamine (12.9 ml) was added dropwise to the resulting mixture, and then ethoxyacetyl chloride (11.34 g) dissolved in anhydrous dichloromethane (50 ml) was added slowly to the resulting mixture, which turned dark. After two hours the dark mixture was allowed to warm to room temperature. TLC analysis of the reaction mixture indicated completion, and the solvent was removed under reduced pressure. The resulting yellow solid was dissolved in chloroform, and the resulting solution was washed with water. The organic layer was dried with magnesium sulfate and concentrated to a dark brown oil (27.75 g) under reduced pressure. NMR analysis of the oil indicated desired product of suitable purity for use in the next step.

Workup

additionwas added slowly to the resulting mixture, which
temperatureto warm to room temperature
customthe solvent was removed under reduced pressure
dissolutionThe resulting yellow solid was dissolved in chloroform
washthe resulting solution was washed with water
dry with materialThe organic layer was dried with magnesium sulfate
concentrationconcentrated to a dark brown oil (27.75 g) under reduced pressure

Sources & evidence

ORD record: ord-ca1589a51e0d4996bf9068ed833c9673
Source dataset: uspto-grants-2004_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06743920B2

Reaction notes

Loading…