Ethylamine → HCID 68486827, compound

HRID 2092226Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[N:13]=[C:12]([C:14]3[CH:19]=[CH:18][N:17]=[C:16](Cl)[CH:15]=3)[N:11]([CH2:21][CH:22]([OH:25])[CH2:23][CH3:24])[N:10]=2)[CH:5]=[CH:6][CH:7]=1.[CH2:26]([NH2:28])[CH3:27]>CO>[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[N:13]=[C:12]([C:14]3[CH:19]=[CH:18][N:17]=[C:16]([NH:28][CH2:26][CH3:27])[CH:15]=3)[N:11]([CH2:21][C@@H:22]([OH:25])[CH2:23][CH3:24])[N:10]=2)[CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 160 °C

Procedure

Intermediate 1-[3-(3-chloro-phenylamino)-5-(2-chloro-pyridin-4-yl)-[1,2,4]triazol-1-yl]-butan-2-ol (prepared according to description 4) (1.15 g; 3.04 mmol) was dissolved in CH3OH (20 ml) and then ethylamine (3 g) was added. The reaction mixture was stirred for 16 hours at 160° C. under pressure (until the reaction had proceeded to completion). The solvent was then evaporated in vacuo. The residue was purified by reversed-phase high-performance liquid chromatography (Shandon Hyperprep® C18 BDS (Base Deactivated Silica) 8 μm, 250 g, I.D. 5 cm). A gradient with 2 mobile phases was applied (phase A: a 0.25% NH4HCO3 solution in water; phase B: CH3CN). The desired fractions were collected, worked-up and finally the residue was crystallized from diisopropyl ether. Yield: 0.1595 g of compound E2 (S-enantiomer).

Workup

customThe solvent was then evaporated in vacuo
customThe residue was purified by reversed-phase high-performance liquid chromatography (Shandon Hyperprep® C18 BDS (Base Deactivated Silica) 8 μm, 250 g, I.D. 5 cm)
customThe desired fractions were collected
customfinally the residue was crystallized from diisopropyl ether

Sources & evidence

ORD record: ord-370d3d382f8c4a8fa8035ecb6fa0f8d7
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08440701B2

Reaction notes

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