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

HRID 1755403Notes

Reaction equation

HRID 1755403 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.C[O:23][C:24]([CH:26]1[CH2:30][CH2:29][NH:28][CH2:27]1)=[O:25].C(N(CC)CC)C.C(=O)([O-])[O-].[Cs+].[Cs+]>>[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:28]3[CH2:29][CH2:30][CH:26]([C:24]([OH:25])=[O:23])[CH2:27]3)[CH:3]=2)=[N:13][C:14]=1[O:20][CH3:21]

Participants

5

Reactant 4

HCID 8471TriethylamineHCID 10796Cesium carbonateHCID 4114360Methyl Pyrrolidine-3-carboxylateHCID 71534334HCID 71534334, compound

Product 1

HCID 866827461-(8-(5,6-Dimethoxypyridin-2-ylamino)imidazo[1,2-b]pyridazin-6-yl)pyrrolidine-3-carboxylic acidYield 6.4%

Conditions

Temperature
180 °C

Procedure

A suspension of 6-chloro-N-(5,6-dimethoxypyridin-2-yl)imidazo[1,2-b]pyridazin-8-amine (1 g, 3.27 mmol), methylpyrrolidine-3-carboxylate (1.69 g, 13.1 mmol), triethylamine (1.32 g, 13.1 mmol) and cesium carbonate (4.26 g, 13.1 mmol) was heated to 180° C. for 2 h. 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)pyrrolidine-3-carboxylic acid (80 mg, 6%) as a red solid. LC-MS: 385 [M+1]+, tR=1.258 min

Workup

  1. customThe residue was purified by chromatography (silica gel, 200-300 mesh, dichloromethane:MeOH=20:1)

Sources & evidence

ORD record
ord-dbb12f9fe06a49019f7bff2b8ae5c0ff
Source dataset
uspto-grants-2015_10
Patent number
US09169259B2

Reaction notes

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