Tyramine → 4-(2-(5-chloro-3-isopropyl-3H-imidazo[4,5-b]pyridin-7-ylamino)ethyl)phenol

HRID 1422499Notes

Reaction equation

[Cl:1][C:2]1[N:7]=[C:6]2[N:8]([CH:11]([CH3:13])[CH3:12])[CH:9]=[N:10][C:5]2=[C:4](Cl)[CH:3]=1.[NH2:15][CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=1>CC(O)C>[Cl:1][C:2]1[N:7]=[C:6]2[N:8]([CH:11]([CH3:13])[CH3:12])[CH:9]=[N:10][C:5]2=[C:4]([NH:15][CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=2)[CH:3]=1

Participants

Conditions

Temperature: 140 °C

Procedure

The product mixture containing 5,7-dichloro-3-isopropyl-3H-imidazo[4,5-b]pyridine (b) (40 mg, 0.17 mmol), tyramine (120 mg, 0.87 mmol), and 2-propanol (2 mL) was heated in a sealed vial at 140° C. for 72 hr. The mixture was concentrated, and the residue was purified by preparative TLC (1:2 hexanes/ethyl acetate eluant) to afford the title compound as an off-white solid. MS m/z 331.1 (M+1).

Workup

concentrationThe mixture was concentrated
customthe residue was purified by preparative TLC (1:2 hexanes/ethyl acetate eluant)

Sources & evidence

ORD record: ord-3c789388075f4d2f8be30e3517a1d9b4
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08927281B2

Reaction notes

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