Methyl piperidine-3-carboxylate → 1-(8-(5,6-Dimethoxypyridin-2-ylamino)imidazo[1,2-b]pyridazin-6-yl)piperidine-3-carboxylic acid

HRID 1755400Notes

Reaction equation

HRID 1755400 reaction equation
Cl[C:2]1[CH:3]=[C:4]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([O:20][CH3:21])[N:13]=2)[C:5]2[N:6]([CH:8]=[CH:9][N:10]=2)[N:7]=1.[NH:22]1[CH2:27][CH2:26][CH2:25][CH:24]([C:28]([O:30]C)=[O:29])[CH2:23]1>>[CH3:19][O:18][C:15]1[CH:16]=[CH:17][C:12]([NH:11][C:4]2[C:5]3[N:6]([CH:8]=[CH:9][N:10]=3)[N:7]=[C:2]([N:22]3[CH2:27][CH2:26][CH2:25][CH:24]([C:28]([OH:30])=[O:29])[CH2:23]3)[CH:3]=2)=[N:13][C:14]=1[O:20][CH3:21]

Participants

3

Reactant 2

HCID 351626Methyl piperidine-3-carboxylateHCID 71534334HCID 71534334, compound

Product 1

HCID 866827441-(8-(5,6-Dimethoxypyridin-2-ylamino)imidazo[1,2-b]pyridazin-6-yl)piperidine-3-carboxylic acidYield 15.4%

Conditions

Temperature
160 °C

Procedure

A suspension of 6-chloro-N-(5,6-dimethoxypyridin-2-yl)imidazo[1,2-b]pyridazin-8-amine (200 mg, 0.65 mmol) and methyl piperidine-3-carboxylate (400 mg, 2.8 mmol) was heated at 160° C. for 2 h under N2. After cooling to room temperature, the residue was purified by chromatography (silica gel, 200-300 mesh, dichloromethane:MeOH=20:1) to give 1-(8-(5,6-dimethoxypyridin-2-ylamino)imidazo[1,2-b]pyridazin-6-yl)piperidine-3-carboxylic acid (40 mg, 15%) as a red solid. LC-MS: 399 [M+1]+, tR=1.261 min.

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe residue was purified by chromatography (silica gel, 200-300 mesh, dichloromethane:MeOH=20:1)

Sources & evidence

ORD record
ord-a4f81b3a6c354eeab4b95cc4ffd82169
Source dataset
uspto-grants-2015_10
Patent number
US09169259B2

Reaction notes

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