1,4-Dioxa-8-azaspiro(4.5)decane → 8-(3-Methyl-[1,2,4]thiadiazol-5-yl)-1,4-dioxa-8-aza-spiro[4.5]decane

HRID 451371

반응식

HRID 451371 반응식
C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2)CCCCC1.[O:26]1[C:30]2([CH2:35][CH2:34][NH:33][CH2:32][CH2:31]2)[O:29][CH2:28][CH2:27]1.Cl[C:37]1[S:41][N:40]=[C:39]([CH3:42])[N:38]=1>O1CCOCC1.[Cl-].[Na+].O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:42][C:39]1[N:38]=[C:37]([N:33]2[CH2:34][CH2:35][C:30]3([O:29][CH2:28][CH2:27][O:26]3)[CH2:31][CH2:32]2)[S:41][N:40]=1

참가 물질

7

반응물 3

HCID 674351,4-Dioxa-8-azaspiro(4.5)decaneHCID 27342162-(Dicyclohexylphosphino)biphenylHCID 129191595-Chloro-3-methyl-1,2,4-thiadiazole

생성물 1

HCID 583979828-(3-Methyl-[1,2,4]thiadiazol-5-yl)-1,4-dioxa-8-aza-spiro[4.5]decane

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 312751,4-Dioxane용매HCID 57417360Sodium chloride; water용매

반응 조건

온도
130 °C

실험 절차

To a prestirred solution (10 minutes at room temperature) of palladium(II) acetate (180 mg, 0.001 mmol) and 2-(dicyclohexylphosphino)biphenyl (572 mg, 0.002 mmol) in dioxane (10 mL) were added 1,4-dioxa-8-azaspiro(4,5)decane (1.3 mL, 10 mmol), 5-chloro-3-methyl-[1,2,4]thiadiazole (1.48 g, 11 mmol) and sodium tert-butylate (1.47 g, 15 mmol) and heated in the microwave at 130° C. for 15 minutes. The reaction mixture was diluted with half saturated brine, the aqueous phase was extracted with ethyl acetate, the combined organic phases were dried over sodium sulfate, the solvent was evaporated and the residue was purified by silica gel chromatography using ethyl acetate as eluent. The title compound was obtained as a light yellow solid (1.87 g, 77%).

후처리

  1. extractionthe aqueous phase was extracted with ethyl acetate
  2. dry with materialthe combined organic phases were dried over sodium sulfate
  3. customthe solvent was evaporated
  4. customthe residue was purified by silica gel chromatography

출처 및 근거

ORD 기록
ord-7ccbc31a04fd4186be31720467f31f27
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08486967B2

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