Triethylamine → HCID 71226938, compound

HRID 2359378Notes

Reaction equation

HRID 2359378 reaction equation
OC(C(F)(F)F)=O.[NH:8]1[C:12]2([CH2:16][CH2:15][O:14][CH2:13]2)[CH2:11][CH2:10][CH2:9]1.C(N(CC)CC)C.[CH3:24][O:25][C:26]1[CH:31]=[CH:30][C:29]([C:32]2[O:36][C:35]([C:37]([N:39]3[CH2:42][CH:41]([O:43][C:44]4[CH:51]=[CH:50][C:47]([CH:48]=O)=[CH:46][CH:45]=4)[CH2:40]3)=[O:38])=[N:34][N:33]=2)=[CH:28][CH:27]=1.[Na].C([O-])(O)=O.[Na+]>ClCCl>[N:8]1([CH2:48][C:47]2[CH:46]=[CH:45][C:44]([O:43][CH:41]3[CH2:42][N:39]([C:37]([C:35]4[O:36][C:32]([C:29]5[CH:30]=[CH:31][C:26]([O:25][CH3:24])=[CH:27][CH:28]=5)=[N:33][N:34]=4)=[O:38])[CH2:40]3)=[CH:51][CH:50]=2)[C:12]2([CH2:16][CH2:15][O:14][CH2:13]2)[CH2:11][CH2:10][CH2:9]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 73554380HCID 73554380, compound

Product 1

HCID 71226938HCID 71226938, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

7-Oxa-1-azaspiro[4.4]nonane TFA salt (0.07 g, 0.29 mmol) was dissolved in dichloromethane (2 ml). Triethylamine (0.044 ml, 0.32 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 finally sodium triacetoxyhydroborate (0.123 g, 0.58 mmol). The mixture was stirred at ambient temperature overnight. The reaction mixture was then diluted with dichloromethane (10 ml) and shaken with NaHCO3 (sat. 3 ml). The two phases were separated by the use of a phase separator. Evaporation of the organic phase afforded a residue, which was purified by preparative reverse-phase HPLC at pH 10 to give 0.072 g (51%) of the desired product as a solid. 1H NMR (600 MHz, DMSO) δ 1.62-1.74 (m, 3H), 1.79-1.9 (m, 2H), 2.10 (dd, 1H), 2.42 (dd, 1H), 2.53-2.55 (m, 1H), 3.41 (d, 1H), 3.48 (d, 1H), 3.63 (d, 1H), 3.69 (q, 1H), 3.80 (d, 1H), 3.88 (s, 3H), 3.91 (td, 1H), 4.09 (dd, 1H), 4.54 (dd, 1H), 4.62 (ddd, 1H), 5.08 (ddd, 1H), 5.15 (ddd, 1H), 6.84 (d, 2H), 7.17-7.21 (m, 2H), 7.25 (d, 2H), 8-8.05 (m, 2H). MS (APCI+) m/z 491.2 [M+H]+, LC purity: 96%

Workup

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

Sources & evidence

ORD record
ord-22356633ff594e7c88a3624c749c8b1e
Source dataset
uspto-grants-2014_04
Patent number
US08685958B2

Reaction notes

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