Triethylamine → HCID 59301307, compound

HRID 2236314Notes

Reaction equation

HRID 2236314 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([N:10]2[CH2:13][CH:12]([OH:14])[CH2:11]2)=[N:8][CH:9]=1)([O-])=O.[C:15]1([C:21]2[O:22][C:23]([C:29]([F:32])([F:31])[F:30])=[C:24]([C:26](O)=[O:27])[N:25]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.CCN(CC)CC.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>CCO.C(O)(=O)C.[Pd]>[OH:14][CH:12]1[CH2:13][N:10]([C:7]2[N:8]=[CH:9][C:4]([NH:1][C:26]([C:24]3[N:25]=[C:21]([C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=4)[O:22][C:23]=3[C:29]([F:31])([F:32])[F:30])=[O:27])=[CH:5][CH:6]=2)[CH2:11]1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 27764382-Phenyl-5-(trifluoromethyl)-oxazole-4-carboxylic acidHCID 529372641-(5-Nitropyridin-2-yl)azetidin-3-ol

Product 1

HCID 59301307HCID 59301307, compoundYield 10.1%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

1-(5-Nitro-pyridin-2-yl)-azetidin-3-ol (400 mg, 2 mmol) was hydrogenated at 35 psi for 2¾ hrs with 10% Pd/C (40 mg) in EtOH (30 mL) and acetic acid (2 drops). The mixture was filtered through a celite plug, evaporated and then co-evaporated with toluene. The residue was dissolved in DMF (15 mL). One half of this solution (7.5 mL, ˜1 mmol) was removed. To this was added 2-phenyl-5-trifluoromethyl-oxazole-4-carboxylic acid (257 mg, 1 mmol), Et3N (422 uL, 3 mmol) and BOP (464 mg. 1.05 mmol). The reaction was stirred for 1 hr at room temperature. Following work-up as above, the crude material was purified by flash chromatography to yield 2-phenyl-5-trifluoromethyl-oxazole-4-carboxylic acid [6-(3-hydroxyazetidin-1-yl)-pyridin-3-yl]-amide as an off-white solid (41 mg). ES-MS calcd for C19H15F3N4O3 (m/e) 404.35, obsd 405.1 (M+H).

Workup

  1. filtrationThe mixture was filtered through a celite plug
  2. customevaporated
  3. dissolutionThe residue was dissolved in DMF (15 mL)
  4. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-ddd055fa484e47ab8238fcef1e46d53f
Source dataset
uspto-grants-2010_05
Patent number
US07714126B2

Reaction notes

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