Triethylamine → 3-{3-[(6-Nitrothieno[3,2-b]pyridin-7-yl)amino]cyclohexyl}acrylonitrile

HRID 712039Notes

Reaction equation

Cl.[NH2:2][CH:3]1[CH2:8][CH2:7][CH2:6][CH:5]([CH:9]=[CH:10][C:11]#[N:12])[CH2:4]1.Cl[C:14]1[C:19]([N+:20]([O-:22])=[O:21])=[CH:18][N:17]=[C:16]2[CH:23]=[CH:24][S:25][C:15]=12.C(N(CC)CC)C>C(O)(C)C>[N+:20]([C:19]1[C:14]([NH:2][CH:3]2[CH2:8][CH2:7][CH2:6][CH:5]([CH:9]=[CH:10][C:11]#[N:12])[CH2:4]2)=[C:15]2[S:25][CH:24]=[CH:23][C:16]2=[N:17][CH:18]=1)([O-:22])=[O:21]

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 3-(3-aminocyclohexyl)acrylonitrile hydrochloride (0.090 g, 0.48 mmol), 7-chloro-6-nitrothieno[3,2-b]pyridine (0.085 g, 0.40 mmol) and triethylamine (0.22 mL, 1.6 mmol) in isopropyl alcohol (0.9 mL) was heated at 90° C. for 1 h. The mixture was concentrated to give the desired product to be used in the next step directly. LCMS calculated for C16H17N4O2 (M+H)+: m/z=329.1. Found: 329.1.

Workup

concentrationThe mixture was concentrated

Sources & evidence

ORD record: ord-4f1ad327ffbd42b096cbbb49504c482e
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181271B2

Reaction notes

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