HCID 178463362, compound → HCID 178463350, compound

HRID 81207Notes

Reaction equation

[Cl:1][C:2]1[C:7]([NH:8][CH:9]([C@H:11]2[CH2:16][CH2:15][C@H:14]([CH3:17])[CH2:13][CH2:12]2)[CH3:10])=[C:6]([NH:18]C(=O)OC(C)(C)C)[CH:5]=[C:4]([Cl:26])[N:3]=1>Cl.O1CCOCC1>[Cl:1][C:2]1[C:7]([NH:8][CH:9]([C@H:11]2[CH2:16][CH2:15][C@H:14]([CH3:17])[CH2:13][CH2:12]2)[CH3:10])=[C:6]([NH2:18])[CH:5]=[C:4]([Cl:26])[N:3]=1

Participants

Conditions

Temperature: 50 °C

Procedure

Crude tert-butyl (2,6-dichloro-3-((1-(trans-4-methylcyclohexyl)ethyl)amino)pyridin-4-yl)carbamate (70 g, 0.17 mol) was dissolved in a solution of HCl in dioxane (550 mL, 4 mol/L). The mixture was heated to 50° C. for 12 h. TLC (petroleum ether/ethyl acetate=5:1) showed the reaction was complete. White solid appeared. The solvent was removed under reduced pressure. The residue was washed with methyl tertiary butyl ether to give crude 2,6-dichloro-N3-(1-(trans-4-methylcyclohexyl)ethyl)pyridine-3,4-diamine, which was used for the next step without further purification. 1H NMR (400 MHz, DMSO-d6) δ: 6.63 (s, 1H), 3.16-3.13 (m, 1H), 1.84-1.76 (m, 2H), 1.67 (bs, 2H), 1.39 (bs, 1H), 1.25 (bs, 1H), 1.10-0.96 (m, 5H), 0.89-0.81 (m, 5H).

Workup

customThe solvent was removed under reduced pressure
washThe residue was washed with methyl tertiary butyl ether

Sources & evidence

ORD record: ord-dd5d5f61dc314b0683c88dfb9d7fa51a
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846657B2

Reaction notes

Loading…