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Potassium Carbonate → 9-[4-(Cycloheptyloxy)phenyl]-3,4-dihydropyrido[2,1-c][1,2,4]thiadiazine 2,2-dioxide

HRID 1622677
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HRID 1622677 반응식
[O:1]=[S:2]1(=[O:19])[CH2:7][CH2:6][N:5]2[CH:8]=[CH:9][CH:10]=[C:11]([C:12]3[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=3)[C:4]2=[N:3]1.C(=O)([O-])[O-].[K+].[K+].Br[CH:27]1[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1.[OH-].[Na+]>CS(C)=O.C1COCC1.CCOC(C)=O>[CH:27]1([O:18][C:15]2[CH:16]=[CH:17][C:12]([C:11]3[C:4]4=[N:3][S:2](=[O:1])(=[O:19])[CH2:7][CH2:6][N:5]4[CH:8]=[CH:9][CH:10]=3)=[CH:13][CH:14]=2)[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1
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참가 물질

8

반응물 4

HCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 16992Bromocycloheptane2회HCID 667478174-(2,2-Dioxido-3,4-dihydropyrido[2,1-c][1,2,4]thiadiazin-9-yl)phenol

생성물 1

HCID 667487069-[4-(Cycloheptyloxy)phenyl]-3,4-dihydropyrido[2,1-c][1,2,4]thiadiazine 2,2-dioxide수율 35.6%

시약·촉매·용매 3

HCID 679Dimethyl Sulfoxide용매
HCID 8028Tetrahydrofuran용매
HCID 8857Ethyl Acetate용매

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온도
130 °C

실험 절차

To a mixture of 4-(2,2-dioxido-3,4-dihydropyrido[2,1-c][1,2,4]thiadiazin-9-yl)phenol (300 mg), potassium carbonate (390 mg) in DMSO (5 mL) was added bromocycloheptane (250 mg). The mixture was stirred at 130° C. for 1 hr. Another bromocycloheptane (100 uL) was added and the mixture was stirred at room temperature overnight. 0.5 N NaOH aq., EtOAc and THF were added and the extracted organic layer was washed with water and brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was crystallized from MeCN/IPE to give the title compound (144 mg) as colorless crystals.

후처리

  1. stirringthe mixture was stirred at room temperature overnight
  2. washthe extracted organic layer was washed with water and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was crystallized from MeCN/IPE

출처 및 근거

ORD 기록
ord-d2be029101de4a8da3ec0d235d86f0f9
출처 데이터셋
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08778934B2

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