Triethylamine → HCID 178441318, compound

HRID 536717Notes

Reaction equation

HRID 536717 reaction equation
[C:1]([C:5]1[O:9][C:8](=[NH:10])[N:7]([CH2:11][C@H:12]2[CH2:16][CH2:15][CH2:14][O:13]2)[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].O.N1(O)C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.[F:40][C:41]1[CH:49]=[CH:48][C:47]([C:50]([F:53])([F:52])[F:51])=[CH:46][C:42]=1[C:43](O)=[O:44].C(N(CC)CC)C>C1COCC1.CCOC(C)=O>[C:1]([C:5]1[O:9]/[C:8](=[N:10]\[C:43](=[O:44])[C:42]2[CH:46]=[C:47]([C:50]([F:51])([F:52])[F:53])[CH:48]=[CH:49][C:41]=2[F:40])/[N:7]([CH2:11][C@H:12]2[CH2:16][CH2:15][CH2:14][O:13]2)[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 6882922-Fluoro-5-(trifluoromethyl)benzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 66643286(r)-5-Tert-butyl-3-((tetrahydrofuran-2-yl)methyl)oxazol-2(3h)-imine

Product 1

HCID 178441318HCID 178441318, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of Example 32B (2 g, 8.92 mmol), 1H-benzo[d][1,2,3]triazol-1-ol hydrate (1.37 g, 8.92 mmol), N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (1.71 g, 8.92 mmol), 2-fluoro-5-(trifluoromethyl)benzoic acid (1.86 g, 8.92 mmol), and triethylamine (1.86 mL, 13.37 mmol) in 30 mL of THF was heated at 80° C. for 12 hr. The mixture was cooled to room temperature, diluted with EtOAc, washed with NaHCO3, dried over MgSO4 and concentrated. The residue was purified by flash chromatography on SiO2 (Hexanes:EtOAc, 0 to 50%) to give the title compound. MS (ESI) m/z 415 (M+H)+.

Workup

  1. washwashed with NaHCO3
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. customThe residue was purified by flash chromatography on SiO2 (Hexanes:EtOAc, 0 to 50%)

Sources & evidence

ORD record
ord-192f3783984f403bba69a2fbd50b88a3
Source dataset
uspto-grants-2014_10
Patent number
US08859596B2

Reaction notes

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