Triethylamine → (3-(4-(2-Oxa-7-azaspiro[4.4]nonan-7-ylmethyl)-3-methylphenoxy)azetidin-1-yl)(5-phenyl-1,3,4-oxadiazol-2-yl)methanone

HRID 2359374노트

반응식

HRID 2359374 반응식
Cl.[CH2:2]1[C:6]2([CH2:10][CH2:9][NH:8][CH2:7]2)[CH2:5][CH2:4][O:3]1.C(N(CC)CC)C.[CH3:18][C:19]1[CH:26]=[C:25]([O:27][CH:28]2[CH2:31][N:30]([C:32]([C:34]3[O:35][C:36]([C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=4)=[N:37][N:38]=3)=[O:33])[CH2:29]2)[CH:24]=[CH:23][C:20]=1[CH:21]=O.[Na].C([O-])(O)=O.[Na+]>ClCCl>[CH2:2]1[C:6]2([CH2:10][CH2:9][N:8]([CH2:21][C:20]3[CH:23]=[CH:24][C:25]([O:27][CH:28]4[CH2:31][N:30]([C:32]([C:34]5[O:35][C:36]([C:39]6[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=6)=[N:37][N:38]=5)=[O:33])[CH2:29]4)=[CH:26][C:19]=3[CH3:18])[CH2:7]2)[CH2:5][CH2:4][O:3]1

참가 물질

7

반응물 5

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 5360545SodiumHCID 580431052-Methyl-4-(1-(5-phenyl-1,3,4-oxadiazole-2-carbonyl)azetidin-3-yloxy)benzaldehydeHCID 717438382-Oxa-7-azaspiro[4.4]nonane hydrochloride

생성물 1

HCID 71225842(3-(4-(2-Oxa-7-azaspiro[4.4]nonan-7-ylmethyl)-3-methylphenoxy)azetidin-1-yl)(5-phenyl-1,3,4-oxadiazol-2-yl)methanone수율 50%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

2-Oxa-7-azaspiro[4.4]nonane HCl salt (0.07 g, 0.43 mmol) was dissolved in dichloromethane (2 ml). Triethylamine (0.064 ml, 0.47 mmol) was added, followed by 2-methyl-4-(1-(5-phenyl-1,3,4-oxadiazole-2-carbonyl)azetidin-3-yloxy)benzaldehyde (0.13 g, 0.36 mmol) and sodium triacetoxyhydroborate (0.152 g, 0.72 mmol). The resulting mixture was stirred at ambient temperature overnight. The reaction mixture was diluted with dichloromethane (10 ml) and then shaken with NaHCO3 (sat. 3 ml). The two phases were separated by the use of a phase separator. Evaporation of the organic phase afforded crude material, which was purified by preparative reverse-phase HPLC at pH 10 to give 85 mg (50%) of the desired product as a solid.

후처리

  1. customThe two phases were separated by the use of a phase separator
  2. customEvaporation of the organic phase
  3. customafforded crude material, which
  4. customwas purified by preparative reverse-phase HPLC at pH 10

출처 및 근거

ORD 기록
ord-eec88a2a85714eb6928298d4cc038a7b
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08685958B2

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