Triethylamine → 5-cyclopropyl-8-methoxy-1-(5-methylisoxazole-3-carbonyl)-2,3,5,6-tetrahydrobenzo[b][1,5]diazocin-4(1H)-one

HRID 1614897노트

반응식

HRID 1614897 반응식
[CH:1]1([N:4]2[C:11](=[O:12])[CH2:10][CH2:9][NH:8][C:7]3[CH:13]=[CH:14][C:15]([O:17][CH3:18])=[CH:16][C:6]=3[CH2:5]2)[CH2:3][CH2:2]1.C(N(CC)CC)C.[CH3:26][C:27]1[O:31][N:30]=[C:29]([C:32](Cl)=[O:33])[CH:28]=1>ClC(Cl)C>[CH:1]1([N:4]2[C:11](=[O:12])[CH2:10][CH2:9][N:8]([C:32]([C:29]3[CH:28]=[C:27]([CH3:26])[O:31][N:30]=3)=[O:33])[C:7]3[CH:13]=[CH:14][C:15]([O:17][CH3:18])=[CH:16][C:6]=3[CH2:5]2)[CH2:2][CH2:3]1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 27368945-Methylisoxazole-3-carbonyl chlorideHCID 529398795-cyclopropyl-8-methoxy-2,3,5,6-tetrahydrobenzo[b][1,5]diazocin-4(1H)-one

생성물 1

HCID 529398825-cyclopropyl-8-methoxy-1-(5-methylisoxazole-3-carbonyl)-2,3,5,6-tetrahydrobenzo[b][1,5]diazocin-4(1H)-one수율 74%

시약·촉매·용매 1

HCID 63651,1-Dichloroethane용매

실험 절차

To a solution of 5-cyclopropyl-8-methoxy-2,3,5,6-tetrahydrobenzo[b][1,5]diazocin-4(1H)-one (50.0 mg, 0.203 mmol) from Example 1 in dichloroethane (2.0 ml) was added triethylamine (0.057 ml, 0.406 mmol) and 5-methylisoxazole-3-carbonyl chloride (32.5 mg, 0.223 mmol). The reaction mixture was stirred at room temperature overnight and then quenched with saturated aqueous sodium bicarbonate, followed by extraction with dichloromethane. The combined organic phases were dried over sodium sulfate, filtered and concentrated. Preparative thin layer chromatography (ethyl acetate/methanol:98/2) of the crude residue gave the desired compound (53 mg, 74%).

후처리

  1. customquenched with saturated aqueous sodium bicarbonate
  2. extractionfollowed by extraction with dichloromethane
  3. dry with materialThe combined organic phases were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-c7f3c11ad5404a5f9df58fbcba1a309c
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08765728B2

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