Diethylamine → HCID 49779046, compound

HRID 1842415Notes

Reaction equation

HRID 1842415 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([CH2:11][O:12][C:13]3[CH:18]=[CH:17][C:16]([C:19]4[C:20](=[O:34])[C:21]([CH3:33])([CH3:32])[O:22][C:23]=4[C:24]4[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=4)=[CH:15][CH:14]=3)[N:10]=2)[N:7]=1.C(NCC)C.[H][H]>CO.[OH-].[Pd+2].[OH-]>[N:10]1[C:9]([CH2:11][O:12][C:13]2[CH:14]=[CH:15][C:16]([C:19]3[C:20](=[O:34])[C:21]([CH3:32])([CH3:33])[O:22][C:23]=3[C:24]3[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=3)=[CH:17][CH:18]=2)=[CH:8][N:6]2[C:5]=1[CH:4]=[CH:3][CH:2]=[N:7]2

Participants

6

Reactant 3

HCID 8021DiethylamineHCID 49778979HCID 49778979, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 49779046HCID 49779046, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

Palladium hydroxide (36 mg) was added to a solution of 4-(4-((6-chloroimidazo[1,2-b]pyridazin-2-yl)methoxy)phenyl)-5-(4-methoxyphenyl)-2,2-dimethylfuran-3(2H)-one (180 mg, 0.37 mmol) and diethyl amine (28 mg, 0.37) in methanol (25 ml) at RT under an atmosphere of nitrogen. The nitrogen atmosphere was exchanged for hydrogen and was stirred at RT for 2 h (the reaction was monitored by TLC). The compound was filtered through a bed of Celite® bed washing with methanol. The filtrate was concentrated under reduced pressure to afford 4-(4-(imidazo[1,2-b]pyridazin-2-ylmethoxy)phenyl)-5-(4-methoxyphenyl)-2,2-dimethylfuran-3(2H)-one (160 mg, 96.7%,) as a white solid. 1H NMR: 500 MHz, DMSO-d6: δ 8.45 (s, 1H), 8.4 (s, 1H) 8.15 (d, 1H), 7.55 (d, 2H), 7.25 (d, 1H), 7.15 (d, 2H), 7.1 (d, 2H), 7.0 (d, 2H), 5.25 (s, 2H) 3.8 (s, 3H), 1.25 (s, 6H). MS: [M+H]+: m/z=442.3. HPLC: (97.4%, Condition-A).

Workup

  1. filtrationThe compound was filtered through a bed of Celite® bed
  2. washwashing with methanol
  3. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-d03162499e4d478da80f60c02cf216fc
Source dataset
uspto-grants-2015_02
Patent number
US08946222B2

Reaction notes

Loading…