Triethylamine → [5-(4-Methoxyphenyl)-1,3,4-oxadiazol-2-yl]-[3-[4-(6-oxa-2-azaspiro[3.4]octan-2-ylmethyl)phenoxy]azetidin-1-yl]methanone

HRID 2359369Notes

Reaction equation

HRID 2359369 reaction equation
Cl.[CH2:2]1[C:5]2([CH2:9][CH2:8][O:7][CH2:6]2)[CH2:4][NH:3]1.C(N(CC)CC)C.[CH3:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[O:29][C:28]([C:30]([N:32]3[CH2:35][CH:34]([O:36][C:37]4[CH:44]=[CH:43][C:40]([CH:41]=O)=[CH:39][CH:38]=4)[CH2:33]3)=[O:31])=[N:27][N:26]=2)=[CH:21][CH:20]=1.[Na].C([O-])(O)=O.[Na+]>ClCCl>[CH2:2]1[C:5]2([CH2:9][CH2:8][O:7][CH2:6]2)[CH2:4][N:3]1[CH2:41][C:40]1[CH:39]=[CH:38][C:37]([O:36][CH:34]2[CH2:35][N:32]([C:30]([C:28]3[O:29][C:25]([C:22]4[CH:23]=[CH:24][C:19]([O:18][CH3:17])=[CH:20][CH:21]=4)=[N:26][N:27]=3)=[O:31])[CH2:33]2)=[CH:44][CH:43]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 5360545SodiumHCID 580430894-(1-(5-(4-Methoxyphenyl)-1,3,4-oxadiazole-2-carbonyl)azetidin-3-yloxy)benzaldehydeHCID 717440076-Oxa-2-azaspiro(3.4)octane hydrochloride

Product 1

HCID 71226277[5-(4-Methoxyphenyl)-1,3,4-oxadiazol-2-yl]-[3-[4-(6-oxa-2-azaspiro[3.4]octan-2-ylmethyl)phenoxy]azetidin-1-yl]methanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

6-Oxa-2-azaspiro[3.4]octane HCl salt (0.052 g, 0.35 mmol) was dissolved in dichloromethane (2 ml). Triethylamine (0.052 ml, 0.38 mmol) was added, followed by 4-(1-(5-(4-methoxyphenyl)-1,3,4-oxadiazole-2-carbonyl)azetidin-3-yloxy)benzaldehyde (0.11 g, 0.29 mmol) and then sodium triacetoxyhydroborate (0.123 g, 0.58 mmol). The reaction was stirred at ambient temperature overnight. The reaction mixture was then diluted with dichloromethane (10 ml), after which it was shaken with NaHCO3 (sat. 2 ml).

Sources & evidence

ORD record
ord-b0ef7ee4883a40ad9bb4fb34d7e95f02
Source dataset
uspto-grants-2014_04
Patent number
US08685958B2

Reaction notes

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