Triethylamine → HCID 71226895, compound

HRID 2359377Notes

Reaction equation

HRID 2359377 reaction equation
OC(C(F)(F)F)=O.[CH2:8]1[C:11]2([CH2:15][CH2:14][CH2:13][NH:12]2)[CH2:10][O:9]1.C(N(CC)CC)C.[C:23]1([C:29]2[O:33][C:32]([C:34]([N:36]3[CH2:39][CH:38]([O:40][C:41]4[CH:48]=[CH:47][C:44]([CH:45]=O)=[CH:43][CH:42]=4)[CH2:37]3)=[O:35])=[N:31][N:30]=2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[Na].C([O-])(O)=O.[Na+]>ClCCl>[CH2:10]1[C:11]2([CH2:15][CH2:14][CH2:13][N:12]2[CH2:45][C:44]2[CH:43]=[CH:42][C:41]([O:40][CH:38]3[CH2:37][N:36]([C:34]([C:32]4[O:33][C:29]([C:23]5[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=5)=[N:30][N:31]=4)=[O:35])[CH2:39]3)=[CH:48][CH:47]=2)[CH2:8][O:9]1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 5360545SodiumHCID 58043115HCID 58043115, compoundHCID 1317312781419590-65-0

Product 1

HCID 71226895HCID 71226895, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2-Oxa-5-azaspiro[3.4]octane TFA salt (0.16 g, 67%, 0.47 mmol) was dissolved in dichloromethane (3 ml). Triethyl amine (0.119 ml, 0.86 mmol) was added, followed by 4-(1-(5-phenyl-1,3,4-oxadiazole-2-carbonyl)azetidin-3-yloxy)benzaldehyde (0.15 g, 0.43 mmol) and finally sodium triacetoxyhydroborate (0.182 g, 0.86 mmol). The mixture was stirred at ambient temperature overnight. The reaction mixture was then diluted with dichloromethane (10 ml) was added 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 colourless residue, which was purified by preparative reverse-phase HPLC at pH 10 to give 0.140 g (73%) of the desired product as a solid. 1H NMR (600 MHz, DMSO) δ 1.62 (dt, 2H), 2.09-2.15 (m, 2H), 2.47-2.5 (m, 2H), 3.90 (d, 2H), 4.08-4.14 (m, 1H), 4.43 (d, 2H), 4.54-4.59 (min, 1H), 4.64 (ddd, 1H), 4.80 (d, 2H), 5.09-5.13 (m, 1H), 5.16 (ddd, 1H), 6.87 (d, 2H), 7.30 (d, 2H), 7.64-7.74 (m, 3H), 8.07-8.13 (m, 2H). MS (APCI+) m/z 447.2 [M+H]+, LC purity: 94%.

Workup

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

Sources & evidence

ORD record
ord-80904ad76fbe48ecbd0ec3a1eb4afe74
Source dataset
uspto-grants-2014_04
Patent number
US08685958B2

Reaction notes

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