Triethylamine → HCID 71227171, compound

HRID 2359382Notes

Reaction equation

HRID 2359382 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.[F:16][CH:17]([F:46])[C:18]1[CH:23]=[CH:22][C:21]([C:24]2[O:28][C:27]([C:29]([N:31]3[CH2:34][CH:33]([O:35][C:36]4[CH:43]=[CH:42][C:39]([CH:40]=O)=[CH:38][C:37]=4[O:44][CH3:45])[CH2:32]3)=[O:30])=[N:26][N:25]=2)=[CH:20][CH:19]=1.C(N(CC)CC)C.[Na].C([O-])(O)=O.[Na+]>ClCCl>[CH2:10]1[C:11]2([CH2:15][CH2:14][CH2:13][N:12]2[CH2:40][C:39]2[CH:42]=[CH:43][C:36]([O:35][CH:33]3[CH2:34][N:31]([C:29]([C:27]4[O:28][C:24]([C:21]5[CH:20]=[CH:19][C:18]([CH:17]([F:46])[F:16])=[CH:23][CH:22]=5)=[N:25][N:26]=4)=[O:30])[CH2:32]3)=[C:37]([O:44][CH3:45])[CH:38]=2)[CH2:8][O:9]1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 5360545Sodium2×HCID 86690184HCID 86690184, compoundHCID 1317312781419590-65-0

Product 1

HCID 71227171HCID 71227171, compoundYield 62.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2-Oxa-5-azaspiro[3.4]octane TFA salt (0.1.1 g, ca. 70%, 0.34 mmol) and 4-(1-(5-(4-(difluoromethyl)phenyl)-1,3,4-oxadiazole-2-carbonyl)azetidin-3-yloxy)-3-methoxybenzaldehyde (0.146 g, 0.34 mmol) were mixed in dichloromethane (2 ml). Triethylamine (0.1 ml, 0.72 mmol) was added, followed by sodium triacetoxyhydroborate (0.144 g, 0.68 mmol). The mixture was stirred at ambient temperature overnight (16 h). LC-MS showed some remaining starting material and an additional amount of sodium triacetoxyhydroborate (0.113 g) was added. Stirring continued for 6 h. 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 0.112 g (62%) of the desired product as a solid.

Workup

  1. stirringStirring
  2. waitcontinued for 6 h
  3. customThe two phases were separated by the use of a phase separator
  4. customEvaporation of the organic phase
  5. customafforded a residue, which
  6. customwas purified by preparative reverse-phase HPLC at pH 10

Sources & evidence

ORD record
ord-54a7929a10ea4dfbb9974f9fe7466191
Source dataset
uspto-grants-2014_04
Patent number
US08685958B2

Reaction notes

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