Methanesulfonyl chloride → HCID 89922440, compound

HRID 921898Notes

Reaction equation

HRID 921898 reaction equation
[Cl:1][C:2]1[C:7]([CH:8]([OH:10])[CH3:9])=[CH:6][C:5]([C:11]#[N:12])=[CH:4][C:3]=1[NH:13][C:14]1[N:19]=[C:18]([NH:20][CH:21]2[CH2:23][CH2:22]2)[C:17]2=[N:24][CH:25]=[C:26]([C:27]#[N:28])[N:16]2[N:15]=1.[CH3:29][S:30](Cl)(=[O:32])=[O:31]>C1COCC1>[CH3:29][S:30]([O:10][CH:8]([C:7]1[CH:6]=[C:5]([C:11]#[N:12])[CH:4]=[C:3]([NH:13][C:14]2[N:19]=[C:18]([NH:20][CH:21]3[CH2:22][CH2:23]3)[C:17]3=[N:24][CH:25]=[C:26]([C:27]#[N:28])[N:16]3[N:15]=2)[C:2]=1[Cl:1])[CH3:9])(=[O:32])=[O:31]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 89923406HCID 89923406, compound

Product 1

HCID 89922440HCID 89922440, compoundYield 101.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-((2-chloro-5-cyano-3-(1-hydroxyethyl)phenyl)amino)-4-(cyclopropylamino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile (Example 677) (56 mg, 0.14 mmol) in THF (4 mL) was cooled in an ice bath and methanesulfonyl chloride (28 μL, 0.36 mmol) was added. The bath was removed and quenched after 5 min with a little water. This was extracted with EtOAc and the organic extracts were washed with brine and dried with sodium sulfate. The solvent was removed to leave 1-(2-chloro-5-cyano-3-((7-cyano-4-(cyclopropylamino)imidazo[2,1-f][1,2,4]triazin-2-yl)amino)phenyl)ethyl methanesulfonate (67 mg) as a white solid that was used as such.

Workup

  1. customThe bath was removed
  2. customquenched after 5 min with a little water
  3. extractionThis was extracted with EtOAc
  4. washthe organic extracts were washed with brine
  5. dry with materialdried with sodium sulfate
  6. customThe solvent was removed

Sources & evidence

ORD record
ord-712c78266bb34edd9f9987cc2af24fcc
Source dataset
uspto-grants-2016_03
Patent number
US09273057B2

Reaction notes

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