Triethylamine → HCID 71226436, compound

HRID 2359379Notes

Reaction equation

HRID 2359379 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.[C:24]1([C:30]2[O:34][C:33]([C:35]([N:37]3[CH2:40][CH:39]([O:41][C:42]4[CH:49]=[CH:48][C:45]([CH:46]=O)=[CH:44][CH:43]=4)[CH2:38]3)=[O:36])=[N:32][N:31]=2)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[Na].C([O-])(O)=O.[Na+]>ClCCl>[N:8]1([CH2:46][C:45]2[CH:44]=[CH:43][C:42]([O:41][CH:39]3[CH2:38][N:37]([C:35]([C:33]4[O:34][C:30]([C:24]5[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=5)=[N:31][N:32]=4)=[O:36])[CH2:40]3)=[CH:49][CH:48]=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 58043115HCID 58043115, compoundHCID 73554380HCID 73554380, compound

Product 1

HCID 71226436HCID 71226436, compoundYield 61%

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-phenyl-1,3,4-oxadiazole-2-carbonyl)azetidin-3-yloxy)benzaldehyde (0.101 g, 0.29 mmol) and finally sodium triacetoxyhydroborate (0.123 g, 0.58 mmol. 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 0.081 g (61%) 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 (dt, 1H), 2.37-2.45 (m, 1H), 2.54 (dd, 1H), 3.41 (d, 1H), 3.48 (d, 1H), 3.63 (d, 1H), 3.69 (q, 1H), 3.80 (d, 1H), 3.91 (td, 1H), 4.10 (dd, 1H), 4.56 (dd, 1H), 4.63 (ddd, 1H), 5.07-5.18 (m, 2H), 6.84 (d, 2H), 7.25 (d, 2H), 7.64-7.73 (m, 3H), 8.08 (dd, 2H). MS (APCI+) m/z 461.2 [M+H]+, LC purity: 97%

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-632e781af9154785aaed8513d518110c
Source dataset
uspto-grants-2014_04
Patent number
US08685958B2

Reaction notes

Loading…