Ethanesulfonylchloride, 2-chloro- → Tak-653

HRID 1405849Notes

Reaction equation

HRID 1405849 reaction equation
[H-].[Na+].Cl[CH2:4][CH2:5][S:6](Cl)(=[O:8])=[O:7].[CH:10]1([O:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]3[C:24]([NH2:30])=[N:25][CH:26]=[C:27]([CH3:29])[N:28]=3)=[CH:19][CH:18]=2)[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1>C1COCC1>[CH:10]1([O:16][C:17]2[CH:18]=[CH:19][C:20]([C:23]3[C:24]4=[N:30][S:6](=[O:8])(=[O:7])[CH2:5][CH2:4][N:25]4[CH:26]=[C:27]([CH3:29])[N:28]=3)=[CH:21][CH:22]=2)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]1

Participants

5

Reactant 3

HCID 15385Ethanesulfonylchloride, 2-chloro-HCID 24758Sodium hydrideHCID 667484133-(4-(Cyclohexyloxy)phenyl)-5-methylpyrazin-2-amine

Product 1

HCID 56655833Tak-653

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of NaH (60%, 100 mg) in THF (dry) (10 mL) was added 2-chloroethanesulfonyl chloride (0.263 mL) at 0° C. and the mixture was stirred for 5 min at the same temperature. A solution of 3-(4-(cyclohexyloxy)phenyl)-5-methylpyrazin-2-amine (236 mg) in THF (dry) (10 mL) was added at 0° C. and the mixture was stirred at room temperature under nitrogen for 15 hr and at 50° C. for 1 hr. The mixture was quenched with water at 0° C. carefully and water was added to form precipitates. The precipitate was crystallized from THF/IPE to give the title compound (128 mg) as yellow crystals.

Workup

  1. stirringthe mixture was stirred at room temperature under nitrogen for 15 hr and at 50° C. for 1 hr
  2. customThe mixture was quenched with water at 0° C. carefully
  3. additionwater was added
  4. customto form
  5. customprecipitates
  6. customThe precipitate was crystallized from THF/IPE

Sources & evidence

ORD record
ord-b020bab034bd42d5ab1811970dec7014
Source dataset
uspto-grants-2014_12
Patent number
US08916551B2

Reaction notes

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