3-(Boc-amino)piperidine → Tert-butyl 1-(8-(5,6-dimethoxypyridin-2-ylamino)imidazo[1,2-b]pyridazin-6-yl)piperidin-3-ylcarbamate

HRID 1755395Notes

Reaction equation

HRID 1755395 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]([NH:28][C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32])[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]([NH:28][C:29](=[O:35])[O:30][C:31]([CH3:33])([CH3:32])[CH3:34])[CH2:23]3)[CH:3]=2)=[N:13][C:14]=1[O:20][CH3:21]

Participants

3

Reactant 2

HCID 42330413-(Boc-amino)piperidineHCID 71534334HCID 71534334, compound

Product 1

HCID 86682739Tert-butyl 1-(8-(5,6-dimethoxypyridin-2-ylamino)imidazo[1,2-b]pyridazin-6-yl)piperidin-3-ylcarbamateYield 15.1%

Conditions

Temperature
160 °C

Procedure

A suspension of 6-chloro-N-(5,6-dimethoxypyridin-2-yl)imidazo[1,2-b]pyridazin-8-amine (1.3 g, 4.24 mmol) and tert-butyl piperidin-3-ylcarbamate (3.4 g, 16.99 mmol) was heated to 160° C. for 2 h. The residue was purified by chromatography (silica gel, 200-300 mesh, dichloromethane:MeOH=120:1) to give the tert-butyl 1-(8-(5,6-dimethoxypyridin-2-ylamino)imidazo[1,2-b]pyridazin-6-yl)piperidin-3-ylcarbamate (300 mg, 15%) as brown solid. LC-MS: 470 [M+1]+, tR=1.44 min

Workup

  1. customThe residue was purified by chromatography (silica gel, 200-300 mesh, dichloromethane:MeOH=120:1)

Sources & evidence

ORD record
ord-f2b2498d0e92488f92315b8fbb790f54
Source dataset
uspto-grants-2015_10
Patent number
US09169259B2

Reaction notes

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