Ethanesulfonylchloride, 2-chloro- → HCID 66749333, compound

HRID 1748062Notes

Reaction equation

HRID 1748062 reaction equation
[H-].[Na+].Cl[CH2:4][CH2:5][S:6](Cl)(=[O:8])=[O:7].[CH3:10][C:11]1([CH3:31])[CH2:16][CH2:15][C:14]([O:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]3[C:25]([NH2:30])=[N:26][CH:27]=[CH:28][CH:29]=3)=[CH:20][CH:19]=2)=[CH:13][CH2:12]1>C1COCC1>[CH3:10][C:11]1([CH3:31])[CH2:16][CH2:15][C:14]([O:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]3[C:25]4=[N:30][S:6](=[O:8])(=[O:7])[CH2:5][CH2:4][N:26]4[CH:27]=[CH:28][CH:29]=3)=[CH:20][CH:19]=2)=[CH:13][CH2:12]1

Participants

5

Reactant 3

HCID 15385Ethanesulfonylchloride, 2-chloro-HCID 24758Sodium hydrideHCID 66749385HCID 66749385, compound

Product 1

HCID 66749333HCID 66749333, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of NaH (60%, 382 mg) in THF (dry) (30 mL) was added 2-chloroethanesulfonyl chloride (0.402 mL) at 0° C. and the mixture was stirred for 10 min at the same temperature. A solution of 3-(4-((4,4-dimethylcyclohex-1-en-1-yl)oxy)phenyl)pyridin-2-amine (563 mg) in THF (dry) (30 mL) was added at 0° C. and the mixture was stirred at room temperature under nitrogen for 3 hr. The mixture was quenched with water at 0° C. Water and EtOAc were added and the mixture was extracted. 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 to give the title compound (369 mg) as a pale yellow solid. A part of the product was crystallized from MeCN/IPE to give a pale yellow crystal.

Workup

  1. stirringthe mixture was stirred at room temperature under nitrogen for 3 hr
  2. customThe mixture was quenched with water at 0° C
  3. additionWater and EtOAc were added
  4. extractionthe mixture was extracted
  5. additionSilica-gel was added to the organic phase
  6. customthe volatiles were removed in vacuo
  7. customwas purified by column chromatography (silica gel, eluted with MeOH in EtOAc)
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cb0d8e21c33a4647afe5c1942da5c5b4
Source dataset
uspto-grants-2015_10
Patent number
US09150591B2

Reaction notes

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