tert-butyl N-(pyrrolidin-3-yl)carbamate → Tert-butyl 1-(8-(5,6-dimethoxypyridin-2-ylamino)imidazo[1,2-b]pyridazin-6-yl)pyrrolidin-3-ylcarbamate

HRID 1755406Notes

Reaction equation

HRID 1755406 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[CH2:26][CH2:25][CH:24]([NH:27][C:28](=[O:34])[O:29][C:30]([CH3:33])([CH3:32])[CH3:31])[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[CH2:26][CH2:25][CH:24]([NH:27][C:28](=[O:34])[O:29][C:30]([CH3:32])([CH3:31])[CH3:33])[CH2:23]3)[CH:3]=2)=[N:13][C:14]=1[O:20][CH3:21]

Participants

3

Reactant 2

HCID 2757234tert-butyl N-(pyrrolidin-3-yl)carbamateHCID 71534334HCID 71534334, compound

Product 1

HCID 86682748Tert-butyl 1-(8-(5,6-dimethoxypyridin-2-ylamino)imidazo[1,2-b]pyridazin-6-yl)pyrrolidin-3-ylcarbamateYield 8.1%

Conditions

Temperature
160 °C

Procedure

A suspension of 6-chloro-N-(5,6-dimethoxypyridin-2-yl)imidazo[1,2-b]pyridazin-8-amine (1.5 g, 4.9 mmol) and tert-butyl pyrrolidin-3-ylcarbamate (3 g, 16 mmol) was heated to 160° C. for 2 h. The residue was purified by chromatography (silica gel, 200-300 mesh, dichloromethane:MeOH=30:1) to give tert-butyl 1-(8-(5,6-dimethoxypyridin-2-ylamino)imidazo[1,2-b]pyridazin-6-yl)pyrrolidin-3-ylcarbamate (180 mg, 8%) as off-white solid. LC-MS: 456 [M+1]+, tR=1.396 min

Workup

  1. customThe residue was purified by chromatography (silica gel, 200-300 mesh, dichloromethane:MeOH=30:1)

Sources & evidence

ORD record
ord-4935955b4d7d47eb8b3932a00efbdef6
Source dataset
uspto-grants-2015_10
Patent number
US09169259B2

Reaction notes

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