Ethanesulfonylchloride, 2-chloro- → HCID 66748070, compound

HRID 1747997Notes

Reaction equation

HRID 1747997 reaction equation
[H-].[Na+].Cl[CH2:4][CH2:5][S:6](Cl)(=[O:8])=[O:7].[F:10][C:11]([F:32])([C:25]1[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][CH:26]=1)[C:12]1[CH:17]=[CH:16][C:15]([C:18]2[C:19]([NH2:24])=[N:20][CH:21]=[CH:22][CH:23]=2)=[CH:14][CH:13]=1>C1COCC1>[F:32][C:11]([F:10])([C:25]1[CH:26]=[CH:27][C:28]([CH3:31])=[CH:29][CH:30]=1)[C:12]1[CH:17]=[CH:16][C:15]([C:18]2[C:19]3=[N:24][S:6](=[O:8])(=[O:7])[CH2:5][CH2:4][N:20]3[CH:21]=[CH:22][CH:23]=2)=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 15385Ethanesulfonylchloride, 2-chloro-HCID 24758Sodium hydrideHCID 66748012HCID 66748012, compound

Product 1

HCID 66748070HCID 66748070, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of NaH (60%, 362 mg) in THF (dry) (20 mL) was added 2-chloroethanesulfonyl chloride (0.571 mL) at 0° C. and the mixture was stirred for 10 min at the same temperature. A solution of 3-(4-(difluoro(4-methylphenyl)methyl)phenyl)pyridin-2-amine obtained by step C of Example 136 in THF (dry) (10 mL) was added at 0° C. and the mixture was stirred at room temperature under a dry atmosphere with anhydrous calcium chloride tube overnight. The mixture was quenched with water/THF then water at 0° C. and extracted with EtOAc/THF. Silica-gel was added to the organic phase and the volatiles were removed in vacuo. The mixture supported on silica-gel was purified by column chromatography (silica gel, eluted with MeOH in EtOAc) and concentrated in vacuo and washed with IPE to give the title compound (197 mg) as an off-white powder. A part of product was recrystallized from MeCN/IPE.

Workup

  1. stirringthe mixture was stirred at room temperature under a dry atmosphere with anhydrous calcium chloride tube overnight
  2. customThe mixture was quenched with water/THF
  3. extractionwater at 0° C. and extracted with EtOAc/THF
  4. additionSilica-gel was added to the organic phase
  5. customthe volatiles were removed in vacuo
  6. customwas purified by column chromatography (silica gel, eluted with MeOH in EtOAc)
  7. concentrationconcentrated in vacuo
  8. washwashed with IPE

Sources & evidence

ORD record
ord-eda4cf03f0544eb68081762146e3d60d
Source dataset
uspto-grants-2015_10
Patent number
US09150591B2

Reaction notes

Loading…