1,2-Dichloroethane → HCID 66598164, compound

HRID 1483791Notes

Reaction equation

HRID 1483791 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([CH2:7][NH:8][C:9]2[CH:10]=[CH:11][C:12]3[N:13]([C:15]([C:18]4[CH:23]=[CH:22][CH:21]=[C:20]([O:24][C:25]([F:28])([F:27])[F:26])[CH:19]=4)=[CH:16][N:17]=3)[N:14]=2)[CH2:3][CH2:2]1.[OH:29][C:30]([CH3:35])([CH3:34])[C:31](O)=[O:32].C(Cl)CCl.C1C=NC2N(O)N=NC=2C=1.CN1CCOCC1>CN(C=O)C.O>[OH:29][C:30]([CH3:35])([CH3:34])[C:31]([N:1]1[CH2:6][CH2:5][CH:4]([CH2:7][NH:8][C:9]2[CH:10]=[CH:11][C:12]3[N:13]([C:15]([C:18]4[CH:23]=[CH:22][CH:21]=[C:20]([O:24][C:25]([F:26])([F:28])[F:27])[CH:19]=4)=[CH:16][N:17]=3)[N:14]=2)[CH2:3][CH2:2]1)=[O:32]

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 116712-Hydroxyisobutyric acidHCID 181649HOAtHCID 57403491HCID 57403491, compound

Product 1

HCID 66598164HCID 66598164, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

Compound N-(piperidin-4-ylmethyl)-3-(3-(trifluoromethoxy)phenyl)imidazo[1,2-b]pyridazin-6-amine (200 mg, 0.47 mmol) was combined with 2-hydroxy-2-methylpropanoic acid (49 mg, 0.47 mmol), EDC (99 mg, 0.51 mmol) and HOAT (64 mg, 0.47 mmol). The mixture was then taken up in DMF (2 mL) and NMM (257 uL, 2.34 mmol) was added. The mixture was then stirred overnight at room temperature. The DMF solution was then poured into an excess of water (20 mL) causing a precipitate to form. The precipitate was collected by filtration and purified via column chromatography (DCM/MeOH 0-15%) to give Compound 2-hydroxy-2-methyl-1-(4-(((3-(3-(trifluoromethoxy)phenyl)imidazo[1,2-b]pyridazin-6-yl)amino)methyl)piperidin-1-yl)propan-1-one.

Workup

  1. customto form
  2. filtrationThe precipitate was collected by filtration
  3. custompurified via column chromatography (DCM/MeOH 0-15%)

Sources & evidence

ORD record
ord-f88686ca7fe44748b0faeb3c3f9f44c6
Source dataset
uspto-grants-2016_08
Patent number
US09416132B2

Reaction notes

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