HCID 89922361, compound → HCID 89922320, compound

HRID 921897Notes

Reaction equation

HRID 921897 reaction equation
[C:1]([C:4]1[C:5]([Cl:28])=[C:6]([NH:12][C:13]2[N:18]=[C:17]([NH:19][CH:20]3[CH2:22][CH2:21]3)[C:16]3=[N:23][CH:24]=[C:25]([C:26]#[N:27])[N:15]3[N:14]=2)[CH:7]=[C:8]([C:10]#[N:11])[CH:9]=1)(=[O:3])[CH3:2].[CH3:29][Mg+].[Br-]>>[Cl:28][C:5]1[C:4]([C:1]([OH:3])([CH3:29])[CH3:2])=[CH:9][C:8]([C:10]#[N:11])=[CH:7][C:6]=1[NH:12][C:13]1[N:18]=[C:17]([NH:19][CH:20]2[CH2:21][CH2:22]2)[C:16]2=[N:23][CH:24]=[C:25]([C:26]#[N:27])[N:15]2[N:14]=1

Participants

3

Reactant 2

HCID 89922361HCID 89922361, compoundHCID 178418689HCID 178418689, compound

Product 1

HCID 89922320HCID 89922320, compoundYield 12.6%

Procedure

A solution of 2-((3-acetyl-2-chloro-5-cyanophenyl)amino)-4-(cyclopropylamino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile (Example 675) (60 mg, 0.15 mmol) in TIIF (8 mL) was cooled in an ice bath and MeMgBr (3 M in THF, 0.26 mL, 0.76 mmol) was added and the reaction was allowed to warm to room temperature. It was quenched with sat. aq. NH4Cl solution and extracted twice with EtOAc. The organic extracts were washed with brine, dried with sodium sulfate, and the solvent removed. HPLC purification afforded 7.7 mg of the title compound,

Workup

  1. customIt was quenched with sat. aq. NH4Cl solution
  2. extractionextracted twice with EtOAc
  3. washThe organic extracts were washed with brine
  4. dry with materialdried with sodium sulfate
  5. customthe solvent removed
  6. customHPLC purification

Sources & evidence

ORD record
ord-95b30c2d423e4c3c955641b80848e636
Source dataset
uspto-grants-2016_03
Patent number
US09273057B2

Reaction notes

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