Dimethyl Sulfoxide → HCID 66603893, compound

HRID 1483801Notes

Reaction equation

HRID 1483801 reaction equation
[NH2:1][CH2:2][CH:3]1[CH2:8][CH2:7]N(CCO)[CH2:5][CH2:4]1.Cl[C:13]1[CH:14]=[CH:15][C:16]2[N:17]([C:19]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([O:28][C:29]([F:32])([F:31])[F:30])[CH:23]=3)=[CH:20][N:21]=2)[N:18]=1.CCN(C(C)C)[CH:36]([CH3:38])[CH3:37].[F-].[Cs+].CS(C)=[O:46]>>[F:30][C:29]([F:32])([F:31])[O:28][C:24]1[CH:23]=[C:22]([C:19]2[N:17]3[N:18]=[C:13]([NH:1][CH2:2][CH:3]4[CH2:4][CH2:5][CH:37]([CH2:36][CH2:38][OH:46])[CH2:7][CH2:8]4)[CH:14]=[CH:15][C:16]3=[N:21][CH:20]=2)[CH:27]=[CH:26][CH:25]=1

Participants

6

Reactant 5

HCID 679Dimethyl SulfoxideHCID 25953Cesium fluorideHCID 81531DiisopropylethylamineHCID 73304762-[4-(Aminomethyl)piperidin-1-yl]ethan-1-olHCID 593798616-Chloro-3-(3-(trifluoromethoxy)phenyl)imidazo[1,2-b]pyridazine

Product 1

HCID 66603893HCID 66603893, compoundYield 8.2%

Conditions

Temperature
120 °C

Procedure

To the solution of compound 2-(4-(aminomethyl)piperidin-1-yl)ethanol (150 mg, 0.95 mmol) and compound 6-chloro-3-(3-(trifluoromethoxy)phenyl)imidazo[1,2-b]pyridazine (200 mg, 0.64 mmol) in 3 mL DMSO was added DIEA (0.3 mL, 1.37 mmol) and 10 mg CsF, the solvent was stirred for 5 h at 120° C., Then the mixture was purified by HPLC to afford the compound 2-(4-(((3-(3-(trifluoromethoxy)phenyl)imidazo[1,2-b]pyridazin-6-yl)amino)methyl)cyclohexyl)ethanol (34 mg, 8.2%) as a brown solid.

Workup

  1. customthe mixture was purified by HPLC

Sources & evidence

ORD record
ord-7b42afefc7254fd6a53346ce504d8777
Source dataset
uspto-grants-2016_08
Patent number
US09416132B2

Reaction notes

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