Ethanesulfonylchloride, 2-chloro- → 9-[6-(Cyclohexyloxy)pyridin-3-yl]-3,4-dihydropyrazino[2,1-c][1,2,4]thiadiazine 2,2-dioxide
Reaction equation
[H-].[Na+].Cl[CH2:4][CH2:5][S:6](Cl)(=[O:8])=[O:7].[CH:10]1([O:16][C:17]2[N:22]=[CH:21][C:20]([C:23]3[C:24]([NH2:29])=[N:25][CH:26]=[CH:27][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[N:22]=[CH:21][C:20]([C:23]3[C:24]4=[N:29][S:6](=[O:8])(=[O:7])[CH2:5][CH2:4][N:25]4[CH:26]=[CH:27][N:28]=3)=[CH:19][CH:18]=2)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a suspension of NaH (60%, 246 mg) in THF (dry) (10 mL) was added 2-chloroethanesulfonyl chloride (0.388 mL) at 0° C. and the mixture was stirred for 10 min at the same temperature. A solution of 3-[6-(cyclohexyloxy)pyridin-3-yl]pyrazin-2-amine (332 mg) in THF (dry) (10 mL) was added at 0° C. and the mixture was stirred at room temperature under nitrogen for 1 day. The mixture was quenched with water at 0° C. carefully. EtOAc and THF were added and the organic layer was separated, washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was crystallized from MeCN-THF/IPE to give the title compound (104 mg) as colorless crystals.
Workup
- stirringthe mixture was stirred at room temperature under nitrogen for 1 day
- customThe mixture was quenched with water at 0° C. carefully
- additionEtOAc and THF were added
- customthe organic layer was separated
- washwashed with brine
- dry with materialdried over anhydrous sodium sulfate
- concentrationconcentrated in vacuo
- customThe residue was crystallized from MeCN-THF/IPE
Sources & evidence
- ORD record
- ord-e2ce22a29d884d2ea3888edd1f93e716
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08778934B2
Reaction notes
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