Pyrrolidine → 6-chloro-N-(6-(pyrrolidin-1-yl)pyridin-2-yl)imidazo[1,2-b]pyridazin-8-amine

HRID 1755290Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14](F)[N:13]=2)[C:5]2[N:6]([CH:8]=[CH:9][N:10]=2)[N:7]=1.[NH:19]1[CH2:23][CH2:22][CH2:21][CH2:20]1>O>[Cl:1][C:2]1[CH:3]=[C:4]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([N:19]3[CH2:23][CH2:22][CH2:21][CH2:20]3)[N:13]=2)[C:5]2[N:6]([CH:8]=[CH:9][N:10]=2)[N:7]=1

Participants

Conditions

Temperature: 205 °C

Procedure

A suspension of 6-chloro-N-(6-fluoropyridin-2-yl)imidazo[1,2-b]pyridazin-8-amine (132 mg, 0.5 mmol) and pyrrolidine (54 mg, 0.75 mmol) in water (0.3 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, CH2Cl2:MeOH=200:1) to give 6-chloro-N-(6-(pyrrolidin-1-yl)pyridin-2-yl)imidazo[1,2-b]pyridazin-8-amine (29 mg, 18%) as a light yellow solid. LC-MS: [M+H]+, 315.0, tR=1.837 min.

Workup

customThe reaction mixture was purified by chromatography (silica gel, 200-300 mesh, CH2Cl2:MeOH=200:1)

Sources & evidence

ORD record: ord-80a00eeb38a94c2e92314df655839e2b
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09169259B2

Reaction notes

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