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 2359374Notes

Reaction equation

HRID 2359374 reaction equation
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

Participants

7

Reactant 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

Product 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)methanoneYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-eec88a2a85714eb6928298d4cc038a7b
Source dataset
uspto-grants-2014_04
Patent number
US08685958B2

Reaction notes

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