Methanesulfonyl chloride → HCID 89922760, compound

HRID 921906Notes

Reaction equation

HRID 921906 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[Cl:6][C:7]1[C:12]([CH2:13][OH:14])=[CH:11][C:10]([C:15]#[N:16])=[CH:9][C:8]=1[NH:17][C:18]1[N:23]=[C:22]([NH:24][CH:25]2[CH2:27][CH2:26]2)[C:21]2=[N:28][CH:29]=[C:30]([C:31]#[N:32])[N:20]2[N:19]=1>C1COCC1>[CH3:1][S:2]([O:14][CH2:13][C:12]1[CH:11]=[C:10]([C:15]#[N:16])[CH:9]=[C:8]([NH:17][C:18]2[N:23]=[C:22]([NH:24][CH:25]3[CH2:27][CH2:26]3)[C:21]3=[N:28][CH:29]=[C:30]([C:31]#[N:32])[N:20]3[N:19]=2)[C:7]=1[Cl:6])(=[O:4])=[O:3]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 89920407HCID 89920407, compound

Product 1

HCID 89922760HCID 89922760, compoundYield 89.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Added methanesulfonyl chloride (0.153 ml, 1.97 mmol) to an ice-cooled solution of 2-((2-chloro-5-cyano-3-(hydroxymethyl)phenyl)amino)-4-(cyclopropylamino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile (300 mg, 0.788 mmol) in THF (20 ml). The bath was removed and after 15 min, water was added and the reaction was extracted with EtOAc. The organic extracts were washed with brine and dried with sodium sulfate. The solvent was removed to leave crude 2-chloro-5-cyano-3-((7-cyano-4-(cyclopropylamino)imidazo[2,1-f][1,2,4]triazin-2-yl)amino)benzyl methanesulfonate (323 mg) as a tan solid

Workup

  1. customThe bath was removed and after 15 min
  2. additionwater was added
  3. extractionthe reaction 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-31ec3b046b504719b42f5bffbd73910b
Source dataset
uspto-grants-2016_03
Patent number
US09273057B2

Reaction notes

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