Pyridine → HCID 86667856, compound

HRID 539780Notes

Reaction equation

HRID 539780 reaction equation
[C:1]([C:3]1[CH:9]=[CH:8][C:7]([C:10]2[N:11]=[C:12]3[CH:17]=[CH:16][C:15]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=4[F:24])=[N:14][N:13]3[CH:25]=2)=[CH:6][C:4]=1[NH2:5])#[CH:2].N1C=CC=CC=1.[CH3:32][C:33]([CH3:38])([CH3:37])[C:34](Cl)=[O:35]>C(#N)C>[C:1]([C:3]1[CH:9]=[CH:8][C:7]([C:10]2[N:11]=[C:12]3[CH:17]=[CH:16][C:15]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=4[F:24])=[N:14][N:13]3[CH:25]=2)=[CH:6][C:4]=1[NH:5][C:34](=[O:35])[C:33]([CH3:38])([CH3:37])[CH3:32])#[CH:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 62493Pivaloyl chlorideHCID 57516208HCID 57516208, compound

Product 1

HCID 86667856HCID 86667856, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 2-ethynyl-5-(6-(2-fluorophenyl)imidazo[1,2-b]pyridazin-2-yl)aniline (0.030 g, 0.0913 mmol) in acetonitrile (1 mL) containing pyridine (0.273 mmol) is added trimethylacetylchloride (0.0958 mmol). The mixture is stirred at room temperature for 4 hours, then concentrated to dryness and residue purified via silica chromatography (hexanes to EtOAc) to afford the title compound (0.029 g, 78%) as a yellow solid: Rf 0.58 (1:1 EtOAc:hexanes); LCMS (m/z)=413.5 [M+H]+, tR=3.19 min. (compound same as Example 321)

Workup

  1. concentrationconcentrated to dryness and residue
  2. custompurified via silica chromatography (hexanes to EtOAc)

Sources & evidence

ORD record
ord-379b5f2554114db3b5d7f9d242cc637c
Source dataset
uspto-grants-2014_10
Patent number
US08871767B2

Reaction notes

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