Triethylamine → 6-(3-Aza-bicyclo[3.1.0]hexan-3-yl)pyridin-2-amine

HRID 1755327Notes

Reaction equation

F[C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[CH:4][CH:3]=1.Cl.[CH:10]12[CH2:15][CH:14]1[CH2:13][NH:12][CH2:11]2.CCN(CC)CC>O>[CH:10]12[CH2:15][CH:14]1[CH2:13][N:12]([C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[CH:4][CH:3]=1)[CH2:11]2

Participants

Conditions

Temperature: 205 °C

Procedure

A suspension of 6-fluoropyridin-2-amine (448 mg, 4 mmol), 3-aza-bicyclo[3.1.0]hexane hydrochloride (576 mg, 4.8 mmol) and Et3N (808 mg, 8 mmol) in water (0.5 mL) was heated to 205° C. in a microwave oven for 30 minutes. The reaction mixture was purified by chromatography (silica gel, 200-300 mesh, petroleum ether:ethyl acetate=10:1) to give 6-(3-aza-bicyclo[3.1.0]hexan-3-yl)pyridin-2-amine (535 mg, 76%) as a colorless oil. LC-MS: [M+H]+, 176.2, tR=1.042 min.

Workup

customThe reaction mixture was purified by chromatography (silica gel, 200-300 mesh, petroleum ether:ethyl acetate=10:1)

Sources & evidence

ORD record: ord-fd4a07f2df9e4e1095cbb6cef5c95045
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09169259B2

Reaction notes

Loading…